4-Methyl-1-piperazinecarbonyl chloride → 3-Fluoro-N-((1-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-4-yl)methyl)-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamide

HRID 1800857Notes

Reaction equation

HRID 1800857 reaction equation
[F:1][C:2]1[C:3]([C:22]([NH:24][CH2:25][C:26]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:23])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=2)=[N:11][CH:10]=1.[CH3:38][N:39]1[CH2:44][CH2:43][N:42]([C:45](Cl)=[O:46])[CH2:41][CH2:40]1>>[F:1][C:2]1[C:3]([C:22]([NH:24][CH2:25][C:26]2([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:27][CH2:28][N:29]([C:45]([N:42]3[CH2:43][CH2:44][N:39]([CH3:38])[CH2:40][CH2:41]3)=[O:46])[CH2:30][CH2:31]2)=[O:23])=[N:4][CH:5]=[CH:6][C:7]=1[S:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=2)=[N:11][CH:10]=1

Participants

3

Reactant 2

HCID 30169354-Methyl-1-piperazinecarbonyl chlorideHCID 250328563-Fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-((4-phenylpiperidin-4-yl)methyl)picolinamide

Product 1

HCID 593213993-Fluoro-N-((1-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-4-yl)methyl)-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamide

Procedure

Following the procedure given for example 81, 3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)-N-((4-phenylpiperidin-4-yl)methyl)picolinamide (compound example 11) was reacted with 4-methylpiperazine-1-carbonyl chloride to give the title compound. LC/MS (M+H)+: 661. Ret. time: 1.46 min. (Condition G); analytical HPLC Ret. time: 6.16 min (Condition H).

Sources & evidence

ORD record
ord-456d1da25231450287966ccd01e0a835
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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