Sodium borohydride → Trifluoroacetic acid

HRID 707137Notes

Reaction equation

HRID 707137 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)[N:12]=[C:11]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]4[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=4)=[O:30])=[CH:24][CH:23]=3)[N:10]=1)[CH2:2]2.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39].[BH4-].[Na+]>CO.O1CCCC1>[OH:21][CH:18]1[CH2:17][CH2:16][N:15]([C:13]2[N:14]=[C:9]([N:3]3[CH2:4][CH:5]4[O:8][CH:1]([CH2:7][CH2:6]4)[CH2:2]3)[N:10]=[C:11]([C:22]3[CH:23]=[CH:24][C:25]([NH:28][C:29]([NH:31][C:32]4[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=4)=[O:30])=[CH:26][CH:27]=3)[N:12]=2)[CH2:20][CH2:19]1.[C:38]([OH:44])([C:40]([F:43])([F:42])[F:41])=[O:39]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86636772HCID 86636772, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44548946HCID 44548946, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-oxopiperidin-1-yl)-1,3,5-triazin-2-yl)phenyl)-3-(pyridin-4-yl)urea-TFA (56 mg) was taken up in methanol/tetrahydrofuran (1:1, 6 mL), and the mixture at 0° C. was treated with sodium borohydride (10 mg). After warming to room temperature, the mixture was concentrated to a residue which then was purified by HPLC to give the title compound as its TFA salt.; MS (ES+) 503.0 (M+H)+

Workup

  1. concentrationthe mixture was concentrated to a residue which
  2. customthen was purified by HPLC

Sources & evidence

ORD record
ord-d61331c0ec554042a9876663fde55c67
Source dataset
uspto-grants-2015_11
Patent number
US09174963B2

Reaction notes

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