tert-Butyl 4-(aminomethyl)-4-(4-fluorophenyl)piperidine-1-carboxylate → Tert-butyl 4-((3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamido)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

HRID 1800845Notes

Reaction equation

HRID 1800845 reaction equation
[F:1][C:2]1[C:3]([C:22]([OH:24])=O)=[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.[NH2:25][CH2:26][C:27]1([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1>>[F:1][C:2]1[C:3]([C:22]([NH:25][CH2:26][C:27]2([C:40]3[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=3)[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]2)=[O:24])=[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 49760833tert-Butyl 4-(aminomethyl)-4-(4-fluorophenyl)piperidine-1-carboxylateHCID 592003973-Fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinic acid2×

Product 1

HCID 59321363Tert-butyl 4-((3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamido)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

Procedure

Following the amide bond forming procedure given in example 37, 3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinic acid (intermediate B in example 1) and tert-butyl 4-(aminomethyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (amine intermediate “P”) were reacted to give the title compound. LC/MS (M+H)+: 653. Ret. time: 2.06 min. (Condition L).

Workup

  1. customforming procedure
  2. customwere reacted

Sources & evidence

ORD record
ord-8188525ebc04450493b909198879935f
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

Loading…