Methanol → HCID 90067635, compound

HRID 1057066Notes

Reaction equation

HRID 1057066 reaction equation
[CH2:1]([N+:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[C:18]([N:20]3[CH2:24][CH2:23][C:22]([F:26])([F:25])[CH2:21]3)[N:17]=[C:16]([NH:27][C:28]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=3)[CH:15]=2)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[C:18]([N:20]3[CH2:24][CH2:23][C:22]([F:26])([F:25])[CH2:21]3)[N:17]=[C:16]([NH:27][C:28]3[CH:33]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:31]=[CH:30][N:29]=3)[CH:15]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 90067517HCID 90067517, compound

Product 1

HCID 90067635HCID 90067635, compound

Conditions

Temperature
25 °C

Procedure

To a solution of 4-(1-benzylpyridin-1-ium-3-yl)-6-(3,3-difluoropyrrolidin-1-yl)-N-[4-(trifluoromethyl)-2-pyridyl]pyridin-2-amine (2-d, 500 mg, 0.9756 mmol) in methyl alcohol (12 ml, 300 equiv., 292.7 mmol) was added sodium borohydride (225 mg, 6.0 equiv., 5.853 mmol) in three portions with the interval of 30 min each, and the reaction was stirred at 25° C. for 4 h. The reaction was quenched by citric acid (10% aq.), and extracted EtOAc three times. After evaporation of the organic layers, the crude brown solid was used without further purification. LCMS: m/z 516 (M+H).

Workup

  1. customThe reaction was quenched by citric acid (10% aq.)
  2. extractionextracted EtOAc three times
  3. customAfter evaporation of the organic layers
  4. customthe crude brown solid was used without further purification

Sources & evidence

ORD record
ord-66cbba8974c847c1acd70dc7621f3eca
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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