HCID 67263940, compound → HCID 66830721, compound

HRID 1041772Notes

Reaction equation

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

Participants

Reactant 2

HCID 67263940HCID 67263940, compound

HCID 87330174HCID 87330174, compound

Product 1

HCID 66830721HCID 66830721, compound

Procedure

Following a procedure analogous to Example 1742a, 8-amino-3-methyl-1,3,4,5-tetrahydro-benzo[d]azepin-2-one and 3-(2,5-dichloro-pyrimidin-4-ylamino)-pyridine-2-carboxylic acid methylamide were converted to 3-[5-chloro-2-(3-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino)-pyrimidin-4-ylamino]-pyridine-2-carboxylic acid methylamide. TFA salt: 1H NMR (300 MHz, CD3OD) δ 8.58 (d, 1H), 8.18 (s, 1H), 7.69 (m, 3H), 7.44 (m, 2H), 7.23 (m, 2H), 6.29 (d, 1H), 4.29 (s, 2H), 3.39 (m, 2H), 3.26 (m, 2H), 3.04 (s, 3H), 2.94 (s, 3H); MS (m/e) 452 (M+1).

Sources & evidence

ORD record: ord-d9772eef538a4822aee29b2272d9b494
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552186B2

Reaction notes

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