Sodium borohydride → HCID 44556080, compound

HRID 221989Notes

Reaction equation

HRID 221989 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]([NH:5][C:6]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:13][CH:12]=2)[CH2:9][C:8](=[O:10])[CH2:7]1)=[O:4].[BH4-].[Na+]>C(Cl)Cl.CO>[F:42][C:2]([F:1])([F:43])[C:3]([NH:5][C:6]1([C:11]2[CH:12]=[CH:13][C:14]([C:17]3[C:26]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[CH:25][C:24]4[C:23]5=[N:33][N:34]=[C:35]([C:36]6[N:41]=[CH:40][CH:39]=[CH:38][N:37]=6)[N:22]5[CH:21]=[CH:20][C:19]=4[N:18]=3)=[CH:15][CH:16]=2)[CH2:9][CH:8]([OH:10])[CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 582298532,2,2-trifluoro-N-(3-oxo-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide

Product 1

HCID 44556080HCID 44556080, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a mixture of 2,2,2-trifluoro-N-(3-oxo-1-{4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-2) (25 mg, 0.043 mmol) in CH2Cl2 (1 mL) and MeOH (1 mL) was added NaBH4 (2.0 mg, 0.052 mmol) at −78° C., and the mixture was stirred at −78° C. for 1 hour. The mixture was quenched with sat. NH4Cl, extracted with CHCl3, washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure to give 2,2,2-trifluoro-N-(3-hydroxy-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-3). MS (M+H)+: observed=581, calculated=581.

Workup

  1. customThe mixture was quenched with sat. NH4Cl
  2. extractionextracted with CHCl3
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f25060e5892a4a5685309d8d781f06dc
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

Loading…