HCID 67264058, compound → HCID 66830076, compound

HRID 1687139Notes

Reaction equation

HRID 1687139 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[CH2:6][CH2:7][N:8]([CH2:11][C@@H:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH2:9][CH2:10][C:4]=2[CH:3]=1.Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:29]=2[C:30]([NH:32][CH3:33])=[O:31])[C:24]([Cl:39])=[CH:23][N:22]=1>>[Cl:39][C:24]1[C:25]([NH:27][C:28]2[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:29]=2[C:30]([NH:32][CH3:33])=[O:31])=[N:26][C:21]([NH:1][C:2]2[CH:19]=[CH:18][C:5]3[CH2:6][CH2:7][N:8]([CH2:11][C@@H:12]([OH:17])[C:13]([F:16])([F:14])[F:15])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:22][CH:23]=1

Participants

3

Reactant 2

HCID 67264058HCID 67264058, compoundHCID 717421912-(2,5-Dichloropyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide

Product 1

HCID 66830076HCID 66830076, compound

Procedure

2-{5-Chloro-2-[3-((R)-3,3,3-trifluoro-2-hydroxy-propyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrimidin-4-ylamino}-3-fluoro-N-methyl-benzamide was prepared from (R)-3-(7-amino-1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-1,1,1-trifluoro-propan-2-ol and 2-(2,5-dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide in an analogous manner to Example 328. Product isolated as a white foam (36 mg, 24%). LCMS (m/e) 553 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 8.78 (s, 1H), 8.09 (s, 1H), 7.38-7.26 (m, 3H), 7.19 (s, 1H), 7.15 (d, 1H, J=8.1 Hz), 6.92 (d, 1H, J=8.1 Hz), 6.86 (s, 1H), 6.15-6.05 (m, 1H), 4.40 (bs, 1H), 4.12-4.00 (m, 1H), 2.94 (d, 3H, J=4.9 Hz), 2.91-2.60 (m, 10H).

Sources & evidence

ORD record
ord-a0db3ea20e8941ca8753fb2a3a74590f
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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