Acetic Acid → HCID 66703732, compound

HRID 425974Notes

Reaction equation

HRID 425974 reaction equation
[BH4-].[Na+].[NH2:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[NH:10][C:11]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:12]=1[C:13]#[N:14].[C:23](O)(=O)[CH3:24]>>[CH2:23]([NH:3][C@@H:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]1[NH:10][C:11]1[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:16]=[CH:15][C:12]=1[C:13]#[N:14])[CH3:24]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 66703684HCID 66703684, compound

Product 1

HCID 66703732HCID 66703732, compound

Conditions

Temperature
60 °C

Procedure

Under ice-cooling, sodium borohydride was slowly added in small portions to an acetic acid solution of 2-{[(1R,2R)-2-aminocyclohexyl]amino}-4-(trifluoromethyl)benzonitrile, followed by heating at 60° C. for 6 hours. By post-treating the reaction liquid, 2-{[(1R,2R)-2-(ethylamino)cyclohexyl]amino}-4-(trifluoromethyl)benzonitrile was obtained. A formalin aqueous solution and sodium triacetoxyborohydride were added to a THF solution of this, followed by stirring. By post-treating the reaction liquid, 2-({(1R,2R)-2-[ethyl(methyl)amino]cyclohexyl}amino)-4-(trifluoromethyl)benzonitrile was obtained.

Workup

  1. temperatureUnder ice-cooling
  2. additionBy post-treating
  3. customthe reaction liquid

Sources & evidence

ORD record
ord-87662124167f419b91b971e4fa38ca01
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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