3-Chloro-4-fluoroaniline → N-(3-Chloro-4-fluorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine

HRID 38562

Reaction equation

HRID 38562 reaction equation
Cl[C:2]1[C:7]2[C:8]3[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][C:9]=3[S:22][C:6]=2[N:5]=[CH:4][N:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[F:31])[NH2:27]>>[Cl:23][C:24]1[CH:25]=[C:26]([NH:27][C:2]2[C:7]3[C:8]4[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][C:9]=4[S:22][C:6]=3[N:5]=[CH:4][N:3]=2)[CH:28]=[CH:29][C:30]=1[F:31]

Participants

3

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 58116846tert-Butyl 4-chloro-5,6,7,9-tetrahydro-8H-pyrimido[5',4':4,5]thieno[2,3-c]azepine-8-carboxylate

Product 1

HCID 58116871N-(3-Chloro-4-fluorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amineYield 82%

Procedure

The title compound was synthesized in analogy to Example 12A from tert-butyl 4-chloro-5,6,7,9-tetrahydro-8H-pyrimido[5′,4′:4,5]thieno[2,3-c]azepine-8-carboxylate from Example 80A (349 mg, 0.40 mmol) and 3-chloro-4-fluoroaniline (61 mg, 0.42 mmol) to yield 169 mg (68% purity, 82% yield), which was used without further purification.

Workup

  1. customto yield 169 mg (68% purity, 82% yield), which
  2. customwas used without further purification

Sources & evidence

ORD record
ord-45612046ffcc475b80dfbb461b510955
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

Loading…