HCID 57853796, compound → HCID 67263577, compound

HRID 1040592Notes

Reaction equation

HRID 1040592 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[C:26]2[NH:27][C:28](=[O:32])[CH2:29][CH2:30][CH2:31][C:25]=2[C:24]([O:33][CH3:34])=[CH:23][CH:22]=1>>[Cl:19][C:5]1[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])=[N:7][C:2]([NH:20][C:21]2[C:26]3[NH:27][C:28](=[O:32])[CH2:29][CH2:30][CH2:31][C:25]=3[C:24]([O:33][CH3:34])=[CH:23][CH:22]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 57853796HCID 57853796, compoundHCID 579741322-(2,5-Dichloropyrimidin-4-ylamino)-N-methylbenzamide

Product 1

HCID 67263577HCID 67263577, compound

Procedure

Analogous to the procedure described in Example 1, the reaction of 2-(2,5-dichloro-pyrimidin-4-ylamino)-N-methyl-benzamide and 9-amino-6-methoxy-1,3,4,5-tetrahydro-benzo[b]azepin-2-one gave 2-[5-chloro-2-(6-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylamino)-pyrimidin-4-ylamino]-N-methyl-benzamide, upon purification by flash chromatography (Dichloromethane: MeOH 97:3) followed by PLC (hexane:EtOAc 1:1), as solid (6%): 1H NMR (400 MHz, CD3OD) δ8.3 (br s, 1H), 7.60 (dd, J=7.70 Hz, 1.44 Hz, 1H), 7.26 (d, J=8.78 Hz, 1H), 7.06 (m, 1H), 7.04 (m, 1H), 6.93 (d, J=8.83 Hz, 1H), 3.89 (s, 3H), 2.90 (s, 3H), 2.82 (m, 2H0, 2.06 (m, 4H); MS (m/e) 467, 468 (M+H);

Sources & evidence

ORD record
ord-65c27c123ce94bb98c75db298b833d2c
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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