Methyl 2-methoxybenzeneacetate → benzyl 4-(6-(2-methoxybenzyl)-4-oxo-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

HRID 2196556Notes

Reaction equation

HRID 2196556 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])[CH2:9][CH2:8]2)[N:5]=[C:4]([C:23]([F:26])([F:25])[F:24])[C:3]=1[C:27](=[O:29])[NH2:28].CO[C:32](=O)[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[O:40][CH3:41].[O-]CC.[Na+]>CCO>[CH3:41][O:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][C:32]1[NH:28][C:27](=[O:29])[C:3]2[C:4]([C:23]([F:26])([F:25])[F:24])=[N:5][N:6]([CH:7]3[CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[O:14])[CH2:11][CH2:12]3)[C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 99590Methyl 2-methoxybenzeneacetateHCID 2723922Sodium ethoxideHCID 59843238benzyl 4-(5-amino-4-carbamoyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 136343919benzyl 4-(6-(2-methoxybenzyl)-4-oxo-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylateYield 22.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 117 (327 mg, 0.795 mmol) in EtOH (3.2 mL) was added 2-Methoxyphenylacetic acid methyl ester (0.26 mL, 1.59 mmol), and then Sodium ethoxide (21% in EtOH, 0.6 mL, 1.59 mmol) and the resulting solution was allowed to stir for 1 h at room temperature, then for 3 h at 75° C. After the usual work-up the crude material was purified via Biotage (10% to 60% EtOAc/Hexane; 12M column) to afford 118 (98 mg, 22.8% yield) as white solid, LRMS (ESI): calc. 541.5; found 542.3 (MH)+.

Workup

  1. waitfor 3 h at 75° C
  2. customAfter the usual work-up the crude material was purified via Biotage (10% to 60% EtOAc/Hexane; 12M column)

Sources & evidence

ORD record
ord-f9461c156c524ddc8284f414c6c21f59
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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