Pyrrolidine → HCID 59809704, compound

HRID 599159Notes

Reaction equation

HRID 599159 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[S:23][C:22]([CH3:24])=[N:21][C:20]=3[CH3:25])[CH:16]=[CH:15][N:14]=2)=[CH:8][CH:7]=1)=[O:4].[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH3:24][C:22]1[S:23][C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:12][C:9]3[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[CH2:2][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:7][CH:8]=3)[N:18]=2)=[C:20]([CH3:25])[N:21]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 9999443HCID 9999443, compound

Product 1

HCID 59809704HCID 59809704, compound

Procedure

By treatment of 2-chloro-N-{4-[4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenyl}-acetamide with pyrrolidine. 1H-NMR (DMSO-D6) δ: d 1.74 (m, 4H, CH2), 2.58 (m, 4H, CH2), 2.61 (s, 3H, CH3), 2.64 (s, 3H, CH3), 3.20 (s, 2H, CH2), 7.04 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 7.55 (d, 2H, J=8.8 Hz, Ph-H), 7.66 (d, 2H, J=8.8 Hz, Ph-H), 8.48 (d, 1H, J=5.4 Hz, pyrimidinyl-H), 9.55 (s, 1H, NH), 9.58 (s, 1H, NH). MS (ESI+) m/z 406.97 [M+H]+ (C21H24N6OS requires 408.52).

Sources & evidence

ORD record
ord-6169c9131ddb420cb4ee7dd9a50d8d7b
Source dataset
uspto-grants-2011_03
Patent number
US07897605B2

Reaction notes

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