4-(Aminomethyl)-4-(4-fluorophenyl)cyclohexan-1-ol → 3-fluoro-N-((1-(4-fluorophenyl)-4-hydroxycyclohexyl)methyl)-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamide

HRID 1800838Notes

Reaction equation

HRID 1800838 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:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1>>[F:1][C:2]1[C:3]([C:22]([NH:25][CH2:26][C:27]2([C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)[CH2:28][CH2:29][CH:30]([OH:33])[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 247300574-(Aminomethyl)-4-(4-fluorophenyl)cyclohexan-1-olHCID 592003973-Fluoro-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinic acid2×

Product 1

HCID 593214373-fluoro-N-((1-(4-fluorophenyl)-4-hydroxycyclohexyl)methyl)-4-(2-(4-methylpyridin-2-ylamino)thiazol-5-ylthio)picolinamide

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 4-(aminomethyl)-4-(4-fluorophenyl)cyclohexanol (amine intermediate “T”) were reacted to give the title compound. LC/MS (M+H)+: 568. Ret. time: 1.51 min. (Condition G); analytical HPLC Ret. time: 8.11 min (Condition H).

Workup

  1. customforming procedure
  2. customwere reacted

Sources & evidence

ORD record
ord-6cd7068dc7c845cb8450d15cc15dcbe4
Source dataset
uspto-grants-2013_01
Patent number
US08343999B2

Reaction notes

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