N-(3,4-Dichlorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine → N-(3,4-Dichlorophenyl)-8-{(2E)-4-[methyl(1-methylethyl)amino]but-2-enoyl}-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amine

HRID 38619Notes

Reaction equation

HRID 38619 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[Cl:8].Cl.[CH3:25][N:26]([CH:33]([CH3:35])[CH3:34])[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]([CH3:25])[CH:33]([CH3:35])[CH3:34])[CH2:18][C:17]=4[S:23][C:14]=3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 58116941N-(3,4-Dichlorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]azepin-4-amineHCID 86650197(2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride

Product 1

HCID 58116797N-(3,4-Dichlorophenyl)-8-{(2E)-4-[methyl(1-methylethyl)amino]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-(3,4-dichlorophenyl)-6,7,8,9-tetrahydro-5H-pyrimido[5′,4′:4,5]thieno[2,3-c]azepin-4-amine from Example 82A (100 mg, 0.27 mmol) and (2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride from Example 2A (74 mg, 0.38 mmol) to yield 71 mg (50%).

Workup

  1. customto yield 71 mg (50%)

Sources & evidence

ORD record
ord-0d72f3780f1c4ef8b94babc9e37efb50
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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