Water → (3,5-bis-trifluoromethyl-benzyl)-[6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-ylmethyl]-carbamic acid methyl ester

HRID 1911733Notes

Reaction equation

HRID 1911733 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:26]([CH3:27])=[N:25][N:24]([CH3:28])[C:12]2=[N:13][C:14]=1[N:15]([CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+].Cl[C:45]([O:47][CH3:48])=[O:46].O>C1COCC1>[CH3:48][O:47][C:45](=[O:46])[N:7]([CH2:6][C:5]1[CH:29]=[C:30]([C:32]([F:34])([F:35])[F:33])[CH:31]=[C:3]([C:2]([F:36])([F:1])[F:37])[CH:4]=1)[CH2:8][C:9]1[CH:10]=[C:11]2[C:26]([CH3:27])=[N:25][N:24]([CH3:28])[C:12]2=[N:13][C:14]=1[N:15]([CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 58689775{5-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl}-cyclopentylmethyl-ethyl-amine

Product 1

HCID 11671498(3,5-bis-trifluoromethyl-benzyl)-[6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-ylmethyl]-carbamic acid methyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {5-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl }-cyclopentylmethyl-ethyl-amine (0.25 g, 0.47 mmol) and potassium carbonate (0.19 g, 1.4 mmol) in THF (10 mL) was stirred for 20 min at RT. Thereafter, methyl chloroformate (0.55 mL, 0.7 mmol) was added and stirring was continued overnight. To this mixture was added water (100 mL) and the product was extracted with ethyl acetate (×30 mL). Theorganic extracts were combined and concentrated and the residue was purified by column chromatography over 230-400 mesh silica gel. Elution with 20% ethyl acetate in hexanes gave the pure product as a colorless, gummy mass (yield: 55%).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionthe product was extracted with ethyl acetate (×30 mL)
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography over 230-400 mesh silica gel
  6. washElution with 20% ethyl acetate in hexanes
  7. customgave the pure product as a colorless, gummy mass (yield: 55%)

Sources & evidence

ORD record
ord-e81847b9fbf6405f8f8b390f13003f23
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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