rac-tert-butyl N-((1R,3S)-3-aminocyclohexyl)carbamate → tert-butyl N-[(1R,3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]cyclohexyl]carbamate

HRID 74926Notes

Reaction equation

HRID 74926 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3]1.[Cl:16][C:17]1[CH:18]=[C:19]2[C:25]([C:26]3[N:31]=[C:30](S(C)=O)[C:29]([F:35])=[CH:28][N:27]=3)=[CH:24][N:23]([S:36]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[C:20]2=[N:21][CH:22]=1>C1COCC1>[Cl:16][C:17]1[CH:18]=[C:19]2[C:25]([C:26]3[N:31]=[C:30]([NH:1][C@H:2]4[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3]4)[C:29]([F:35])=[CH:28][N:27]=3)=[CH:24][N:23]([S:36]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[C:20]2=[N:21][CH:22]=1

Participants

4

Reactant 2

HCID 59710757rac-tert-butyl N-((1R,3S)-3-aminocyclohexyl)carbamateHCID 672853215-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

Product 1

HCID 68007892tert-butyl N-[(1R,3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]cyclohexyl]carbamateYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl N-[(1R,3S)-3-aminocyclohexyl]carbamate, 20a, (0.15 g, 0.70 mmol) and 5-chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine, 1a, (0.49 g, 1.05 mmol) were dissolved in THF (30 mL) and allowed to stir at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was purified by two rounds of silica gel chromatography—first with (0%-10% MeOH/CH2Cl2) second with (10%-50% EtOAc/hexanes) to provide tert-butyl N-[(1R,3S)-3-[[2-[5-chloro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]-5-fluoro-pyrimidin-4-yl]amino]cyclohexyl]carbamate (20b) (330 mg, 38%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by two rounds of silica gel chromatography—first with (0%-10% MeOH/CH2Cl2) second with (10%-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2cc05aeabdc0479996cf35ad97f7eee3
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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