N-[1-(3-Fluorobenzyl)-1H-indazol-5-yl]-6,7,8,9-tetrahydro-5H-pyrimido[5',4':4,5]thieno[2,3-c]-azepin-4-amine → N-[1-(3-Fluorobenzyl)-1H-indazol-5-yl]-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 38622Notes

Reaction equation

HRID 38622 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]4[C:22]5[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][C:23]=5[S:29][C:20]=4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1.Cl.[CH3:34][N:35]([CH:42]([CH3:44])[CH3:43])[CH2:36]/[CH:37]=[CH:38]/[C:39](O)=[O:40]>>[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16]3[C:21]4[C:22]5[CH2:28][CH2:27][CH2:26][N:25]([C:39](=[O:40])/[CH:38]=[CH:37]/[CH2:36][N:35]([CH3:34])[CH:42]([CH3:44])[CH3:43])[CH2:24][C:23]=5[S:29][C:20]=4[N:19]=[CH:18][N:17]=3)=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

3

Reactant 2

HCID 58116853N-[1-(3-Fluorobenzyl)-1H-indazol-5-yl]-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 25222662N-[1-(3-Fluorobenzyl)-1H-indazol-5-yl]-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-[1-(3-fluorobenzyl)-1H-indazol-5-yl]-6,7,8,9-tetrahydro-5H-pyrimido[5′,4′:4,5]thieno[2,3-c]azepin-4-amine from Example 83A (100 mg, 0.23 mmol) and (2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride from Example 2A (61 mg, 0.32 mmol) to yield 39 mg (29%).

Workup

  1. customto yield 39 mg (29%)

Sources & evidence

ORD record
ord-b9ae40194f5b44ada4c454ed3eb4ff7b
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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