4-Bromocrotonic acid → 8-{(2E)-4-[Cyclopropyl(methyl)amino]but-2-enoyl}-N-(3,4-dichlorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine

HRID 38620

Reaction equation

HRID 38620 reaction equation
Br[CH2:2]/[CH:3]=[CH:4]/[C:5]([OH:7])=O.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:22]3[C:23]4[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][C:24]=4[S:30][C:21]=3[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[Cl:15].[CH3:31][NH:32][CH:33]1[CH2:35][CH2:34]1>>[CH:33]1([N:32]([CH3:31])[CH2:2]/[CH:3]=[CH:4]/[C:5]([N:26]2[CH2:27][CH2:28][CH2:29][C:23]3[C:22]4[C:17]([NH:16][C:11]5[CH:12]=[CH:13][C:14]([Cl:15])=[C:9]([Cl:8])[CH:10]=5)=[N:18][CH:19]=[N:20][C:21]=4[S:30][C:24]=3[CH2:25]2)=[O:7])[CH2:35][CH2:34]1

Participants

4

Reactant 3

HCID 64364114-Bromocrotonic acidHCID 11029756N-MethylcyclopropanamineHCID 58116941N-(3,4-Dichlorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine

Product 1

HCID 252209938-{(2E)-4-[Cyclopropyl(methyl)amino]but-2-enoyl}-N-(3,4-dichlorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine

Procedure

In analogy to Example 130, the title compound was prepared from (2E)-4-bromobut-2-enoic acid (127 mg, 0.62 mmol), N-(3,4-dichlorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5′,4′:4,5]thieno[2,3-c]azepin-4-amine from Example 82A (150 mg, 0.41 mmol) and N-methylcyclopropanamine (116 mg, 1.63 mmol) to yield 21 mg (10%).

Workup

  1. customto yield 21 mg (10%)

Sources & evidence

ORD record
ord-8f5fca2e8f3b44728c6d2cc1c9ec8754
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

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