7-Amino-1,1-dimethyl-1,2,4,5-tetrahydrobenzo[c]azepin-3-one → 3-(5-Chloro-2-(1,1-dimethyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-ylamino)pyrimidin-4-ylamino)-N-methylthiophene-2-carboxamide

HRID 1688120Notes

Reaction equation

HRID 1688120 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]([CH3:13])([CH3:12])[NH:7][C:8](=[O:11])[CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:17]1[N:22]=[C:21]([NH:23][C:24]2[C:28](C)=[CH:27][S:26][C:25]=2[C:30]([NH:32][CH3:33])=[O:31])[C:20]([Cl:34])=[CH:19][N:18]=1>>[Cl:34][C:20]1[C:21]([NH:23][C:24]2[CH:28]=[CH:27][S:26][C:25]=2[C:30]([NH:32][CH3:33])=[O:31])=[N:22][C:17]([NH:1][C:2]2[CH:15]=[CH:14][C:5]3[C:6]([CH3:13])([CH3:12])[NH:7][C:8](=[O:11])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 672644267-Amino-1,1-dimethyl-1,2,4,5-tetrahydrobenzo[c]azepin-3-oneHCID 866340193-(2,5-dichloropyrimidin-4-ylamino)-N,4-dimethylthiophene-2-carboxamide

Product 1

HCID 672638683-(5-Chloro-2-(1,1-dimethyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-ylamino)pyrimidin-4-ylamino)-N-methylthiophene-2-carboxamide

Procedure

Following a procedure analogous to Example 1826d, 7-amino-1,1-dimethyl-1,2,4,5-tetrahydrobenzo[c]azepin-3-one and 3-(2,5-dichloropyrimidin-4-ylamino)-N,4-dimethylthiophene-2-carboxamide were converted to 3-(5-chloro-2-(1,1-dimethyl-3-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-ylamino)pyrimidin-4-ylamino)-N-methylthiophene-2-carboxamide, TFA salt: 1H NMR (300 MHz, CD3OD) δ 8.2 (s, 1H), 7.4 (d, 1H), 7.3 (d, 1H), 7.25 (d, 1H), 7.1 (dd, 1H), 3.0 (m, 2H), 2.8 (s, 3H), 2.6 (m, 2H), 2.1 (s, 3H) 1.7 (s, 6H).

Sources & evidence

ORD record
ord-d1de4f7015a24a7ca0bc37f41a29546a
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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