Method for producing benzo annelated heterocycles
AssigneeMerck Patent GmbH
InventorsFrank-Hardi Wartenberg, Thomas Koppe, Walter Wetzel, Markus Wydra, Achim Benz
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Abstract
Process for the preparation of benzo-fused heterocycles of general formula I: 1 in which X, R1, R2, R3, R4, R5 and n are as defined in claim 1, by reacting tetrahydrobenzo-fused heterocycles of formula II: in which X, R1, R2, R3, R4, R5, n and Ac are as defined in claim 1, with a catalytic amount of a noble metal catalyst in the presence of a hydrogen acceptor and then deacylating the acylated amino group by the addition of an amine.
Claims11
Process for the preparation of benzo-fused heterocycles of general formula I:
- 4
- in which
- X is S, O or NH,
- R1 is CN, NO2, Ac, COAr, COOAr, COOH, COOA or CONR4R5,
- R2 and R3 independently of one another are each H, A, NO2, CN, OH, OA or Ac,
- R4 and R5 independently of one another are each H, A, Ar or Ac, or
- R4 and R5 together are —(CH2)—(CH2)n—(CH2)—,
- A is alkyl having 1-6 C atoms,
- Ac is acyl having 1-6 C atoms,
- Ar is unsubstituted phenyl or phenyl substituted by A, NO2, CN, OH or OA, and
- n is 2, 3 or 4,
- by reacting tetrahydrobenzo-fused heterocycles of formula II:
- 5
- in which
- X is S, O or NH,
- R1 is CN, NO2, Ac, COAr, COOAr, COOH, COOA or CONR4R5,
- R2 and R3 independently of one another are each H, A, NO2, CN, OH, OA or Ac,
- R4 and R5 independently of one another are each H, A, Ar or Ac, or
- R4 and R5 together are —(CH2)—(CH2)n—(CH2)—,
- A is alkyl having 1-6 C atoms,
- Ac is acyl having 1-6 C atoms,
- Ar is unsubstituted phenyl or phenyl substituted by A, NO2, CN, OH or OA, and
- n is 2, 3 or 4,
- with a catalytic amount of a noble metal-catalyst in the presence of a hydrogen acceptor and then deacylating the acylated amino group by the addition of an amine.
Use of methyl or ethyl 2-aminobenzo[b]thiophene-3-carboxylate as an intermediate in the synthesis of 4-[4-(3-chloro-4-methoxybenzylamino)benzo[4,5]thieno[2,3-d]pyrimidin-2-yl]cyclohexanecarboxylic acid.
Use of methyl or ethyl 2-aminobenzo[b]thiophene-3-carboxylate as an intermediate in the synthesis of 4-[4-(3-chloro-4-hydroxybenzylamino)benzo[4,5]thieno[2,3-d]pyrimidin-2-yl]cyclohexanecarboxylic acid.
Dependencies are inferred from the claim text.