Acetic Acid → HCID 71539739, compound

HRID 1466210Notes

Reaction equation

HRID 1466210 reaction equation
C(O)(=O)C.[CH:5]1([CH2:8][N:9]([CH2:26][CH:27]2[CH2:29][CH2:28]2)[C:10]2[N:15]=[C:14]3[N:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[N:17]=[C:18]([CH3:19])[C:13]3=[CH:12][C:11]=2[CH:24]=O)[CH2:7][CH2:6]1.[F:30][C:31]([F:45])([F:44])[C:32]1[CH:33]=[C:34]([CH2:42][NH2:43])[CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1.C([BH3-])#N.[Na+]>CO>[F:30][C:31]([F:44])([F:45])[C:32]1[CH:33]=[C:34]([CH:35]=[C:36]([C:38]([F:41])([F:39])[F:40])[CH:37]=1)[CH2:42][NH:43][CH2:24][C:11]1[CH:12]=[C:13]2[C:18]([CH3:19])=[N:17][N:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]2=[N:15][C:10]=1[N:9]([CH2:26][CH:27]1[CH2:29][CH2:28]1)[CH2:8][CH:5]1[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 89480352HCID 89480352, compound

Product 1

HCID 71539739HCID 71539739, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (2.82 g, 46 mmol) was added to a mixture of 6-(bis(cyclopropylmethyl)amino)-1-(tert-butyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (8 g, 23 mmol) and (3,5-bis(trifluoromethyl)phenyl)methanamine (5.7 g, 23 mmol) in methanol at 0° C. The resulting mixture was stirred continuously for 20 min. Sodium cyanoborohydride (4.5 g, 70 mmol) was added portion wise to the reaction mixture at 0° C. and the mixture was stirred for 1 h. After which the mixture was quenched with water, organic layer was separated, washed with brine, dried and evaporated to obtain the title compound.

Workup

  1. stirringthe mixture was stirred for 1 h
  2. customAfter which the mixture was quenched with water, organic layer
  3. customwas separated
  4. washwashed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-651f88bba5024c8eabf40b88229959ac
Source dataset
uspto-grants-2015_04
Patent number
US09000007B2

Reaction notes

Loading…