HCID 118322699, compound → HCID 90159395, compound

HRID 629807Notes

Reaction equation

HRID 629807 reaction equation
[CH2:1]([O:3][C:4](=[O:45])[CH2:5][NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[C:11]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[N:23]([CH2:38][CH2:39][N:40]4[CH2:44][CH2:43][CH2:42][CH2:41]4)[CH:24]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=4)[N:26]=3)[CH2:18][CH2:17]2)[N:10]=[CH:9][N:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:45])[CH2:5][NH:6][C:7]1[C:12]([NH2:13])=[C:11]([N:16]2[CH2:17][CH2:18][CH:19]([C:22]3[N:23]([CH2:38][CH2:39][N:40]4[CH2:44][CH2:43][CH2:42][CH2:41]4)[CH:24]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=4)[N:26]=3)[CH2:20][CH2:21]2)[N:10]=[CH:9][N:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 118322699HCID 118322699, compound

Product 1

HCID 90159395HCID 90159395, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of (6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-5-nitro-pyrimidin-4-ylamino)-acetic acid ethyl ester (30.00 mg; 0.05 mmol; 1.00 eq.), and Pd/C (100 mg) in MeOH (10 mL) was hydrogenated under 20 psi for 2 hours. After filtration, the solvent was removed to yield (5-amino-6-{4-[4-(4-fluoro-3-trifluoromethyl-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidin-4-ylamino)-acetic acid ethyl ester (25 mg, 87% yield), which was used for the next reaction; LC/MS: 605 (M+H)

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-fcc1016079784ec7bcc4f846e44a8c7a
Source dataset
uspto-grants-2016_04
Patent number
US09315517B2

Reaction notes

Loading…