HCID 67263979, compound → HCID 66829513, compound

HRID 1041300Notes

Reaction equation

HRID 1041300 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]2[N:5]([CH:6]=[CH:7][N:8]=2)[C:4]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:3]1=2.Cl[C:19]1[N:24]=[C:23]([NH:25][C:26]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:27]=2[C:28]([NH:30][CH3:31])=[O:29])[C:22]([Cl:37])=[CH:21][N:20]=1>>[Cl:37][C:22]1[C:23]([NH:25][C:26]2[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:27]=2[C:28]([NH:30][CH3:31])=[O:29])=[N:24][C:19]([NH:16][C:13]2[CH:14]=[CH:15][C:3]3[C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10][C:9]4[N:5]([CH:6]=[CH:7][N:8]=4)[C:4]=3[CH:12]=2)=[N:20][CH:21]=1

Participants

3

Reactant 2

HCID 67263979HCID 67263979, compoundHCID 717421912-(2,5-Dichloropyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide

Product 1

HCID 66829513HCID 66829513, compound

Procedure

2-[5-Chloro-2-(6,6-dimethyl-5,6-dihydro-4H-3,10b-diaza-benz[e]azulen-9-ylamino)-pyrimidin-4-ylamino]-3-fluoro-N-methyl-benzamide was prepared from 6,6-Dimethyl-5,6-dihydro-4H-3,10b-diaza-benz[e]azulen-9-ylamine and 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide in an analogous manner to Example 1223c. Title compound was isolated as a white solid (64 mg, 42%) LCMS 506.22 (M+H), HPLC purity 99%, 1H-NMR (DMSO-d6, 400 MHz) δ 9.69 (s, 1H), 9.38 (s, 1H), 8.47 (m, 1H), 8.23 (s, 1H), 7.80 (d, J=6.3 Hz, 1H), 7.72 (s, 1H), 7.55 (s, 1H), 7.40 (d, J=7.5 Hz, 1H), 7.34 (d, J=8.8 Hz, 1H), 7.28-7.23 (m, 2H), 2.92 (m, 2H), 2.74 (d, J=4.4 Hz, 3H), 2.15 (m, 2H).

Sources & evidence

ORD record
ord-a72719c9c93e4a1698c4ae464a41e7f4
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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