3,5-Bis(trifluoromethyl)benzylamine → {5-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl}-cyclopentylmethyl-ethyl-amine

HRID 1911732Notes

Reaction equation

HRID 1911732 reaction equation
[CH:1]1([CH2:6][N:7]([CH2:21][CH3:22])[C:8]2[N:13]=[C:12]3[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][C:9]=2[CH:19]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:23][C:24]([F:38])([F:37])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:28][NH2:29].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[F:23][C:24]([F:37])([F:38])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:32]=1)[CH2:28][NH:29][CH2:19][C:9]1[CH:10]=[C:11]2[C:16]([CH3:17])=[N:15][N:14]([CH3:18])[C:12]2=[N:13][C:8]=1[N:7]([CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 574868046-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

Product 1

HCID 58689775{5-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl}-cyclopentylmethyl-ethyl-amineYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (5.3 g, 17.0 mmol) and 3,5-bis-trifluoromethylbenzylamine (4.7 g, 0.019 mol) in MeOH and acetic acid (2 drops) was stirred at RT for 30 min. After cooling to 0° C., sodium cyanoborohydride (2.2 g, 35.0 mmol) was added slowly over a period of about 10 min. After stirring atRT for 30 min, the reaction mixture was concentrated in vacuo. Water (50 mL) was added to the residue and stirred for 30 min. The solid was filtered off, washed with water followed by petroleum ether, and dried in vacuo to yield colorless solid (yield: 72%).

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringAfter stirring atRT for 30 min
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additionWater (50 mL) was added to the residue
  5. stirringstirred for 30 min
  6. filtrationThe solid was filtered off
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-4277fea63dd74b5791b5886403b9e4e0
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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