HCID 67263963, compound → HCID 57392000, compound

HRID 1687673Notes

Reaction equation

HRID 1687673 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]([CH3:21])([CH3:20])[CH2:7][CH:8]([NH:12][C:13]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[O:14])[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.Cl[C:25]1[N:30]=[C:29]([NH:31][C:32]2[C:41]([F:42])=[CH:40][CH:39]=[CH:38][C:33]=2[C:34]([NH:36][CH3:37])=[O:35])[C:28]([Cl:43])=[CH:27][N:26]=1>>[Cl:43][C:28]1[C:29]([NH:31][C:32]2[C:33]([C:34](=[O:35])[NH:36][CH3:37])=[CH:38][CH:39]=[CH:40][C:41]=2[F:42])=[N:30][C:25]([NH:1][C:2]2[CH:23]=[CH:22][C:5]3[C:6]([CH3:20])([CH3:21])[CH2:7][CH:8]([NH:12][C:13]([N:15]4[CH2:19][CH2:18][CH2:17][CH2:16]4)=[O:14])[C:9](=[O:11])[NH:10][C:4]=3[CH:3]=2)=[N:26][CH:27]=1

Participants

3

Reactant 2

HCID 67263963HCID 67263963, compoundHCID 717421912-(2,5-Dichloropyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide

Product 1

HCID 57392000HCID 57392000, compound

Procedure

Pyrrolidine-1-carboxylic acid {8-[5-chloro-4-(2-fluoro-6-methylcarbamoyl-phenylamino)-pyrimidin-2-ylamino]-5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl}-amide was prepared from Pyrrolidine-1-carboxylic acid (8-amino-5,5-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-amide and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide in an analogous manner to Example 1221d. Title compound was isolated as a white solid (29 mg, 22%), HPLC purity=94%, LCMS 597 (M+H), 1H-NMR (DMSO-d6, 400 MHz) δ 9.47 (s, 1H), 9.40 (s, 1H), 9.33 (s, 1H), 8.54 (d, 1H), 8.19 (s, 1H), 7.52-7.42 (m, 2H), 7.38-7.25 (m, 2H), 7.15-7.07 (m, 2H), 5.92 (m, 1H), 4.09 (m, 1H), 3.22-3.18 (m, 4H), 2.73 (d, J=3.5 Hz, 3H), 1.81-1.77 (m, 4H), 1.32 (s, 3H), 1.23 (s, 3H).

Sources & evidence

ORD record
ord-914d4a07103147f7976db1316a61acdd
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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