(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride → N-(3-Chloro-4-fluorophenyl)-8-[(2E)-4-(dimethylamino)but-2-enoyl]-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine

HRID 38618Notes

Reaction equation

HRID 38618 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3[C:16]4[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][C:17]=4[S:23][C:14]=3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl.[CH3:25][N:26]([CH3:33])[CH2:27]/[CH:28]=[CH:29]/[C:30](O)=[O:31]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3[C:16]4[CH2:22][CH2:21][CH2:20][N:19]([C:30](=[O:31])/[CH:29]=[CH:28]/[CH2:27][N:26]([CH3:33])[CH3:25])[CH2:18][C:17]=4[S:23][C:14]=3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 58116871N-(3-Chloro-4-fluorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine

Product 1

HCID 58116798N-(3-Chloro-4-fluorophenyl)-8-[(2E)-4-(dimethylamino)but-2-enoyl]-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine

Procedure

The title compound was synthesized in analogy to Example 89 from N-(3-chloro-4-fluorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5′,4′:4,5]thieno[2,3-c]azepin-4-amine from Example 81A (160 mg, 80% purity, 0.37 mmol) and (2E)-4-(dimethylamino)but-2-enoic acid hydrochloride from Example 1A (85 mg, 0.51 mmol) to yield 12 mg (7%).

Workup

  1. customto yield 12 mg (7%)

Sources & evidence

ORD record
ord-49a83f62879b4e14b397ee9b367f412e
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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