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 577768Notes

Reaction equation

HRID 577768 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 ester

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 (3×100 mL). The organic 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 (55%).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. extractionthe product was extracted with ethyl acetate (3×100 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 (55%)

Sources & evidence

ORD record
ord-dcd8699dee2c40e898a8ba3a40356c12
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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