3-Fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinic acid → Tert-butyl 4-(2,4-difluorophenyl)-4-((3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamido)methyl)piperidine-1-carboxylate

HRID 1800846Notes

Reaction equation

HRID 1800846 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][C:41]=2[F:47])[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:47][C:41]1[CH:42]=[C:43]([F:46])[CH:44]=[CH:45][C:40]=1[C:27]1([CH2:26][NH:25][C:22](=[O:24])[C:3]2[C:2]([F:1])=[C:7]([S:8][C:9]3[S:13][C:12]([NH:14][C:15]4[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=4)=[N:11][CH:10]=3)[CH:6]=[CH:5][N:4]=2)[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 592003973-Fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinic acid2×HCID 59321416Tert-butyl 4-(aminomethyl)-4-(2,4-difluorophenyl)piperidine-1-carboxylate

Product 1

HCID 59321414Tert-butyl 4-(2,4-difluorophenyl)-4-((3-fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamido)methyl)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-(2,4-difluorophenyl)piperidine-1-carboxylate (amine intermediate “Q”) were reacted to give the title compound. LC/MS (M+H)+: 671. Ret. time: 2.07 min. (Condition L).

Workup

  1. customforming procedure
  2. customwere reacted

Sources & evidence

ORD record
ord-161a4156d5474a96afa3f9f83f623fe2
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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