Water → tert-butyl N-cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate

HRID 2253387

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[N:19]2[N:20]=[C:21]([CH2:31][O:32][CH3:33])[C:22]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:18]2[CH:17]=[CH:16][CH:15]=1.[H-].[Na+].Br[CH2:37][CH:38]1[CH2:40][CH2:39]1.O>CN(C)C=O.C(OCC)(=O)C>[CH:38]1([CH2:37][N:23]([C:22]2[C:21]([CH2:31][O:32][CH3:33])=[N:20][N:19]3[C:14]([C:4]4[C:5]([O:12][CH3:13])=[CH:6][C:7]([CH2:9][O:10][CH3:11])=[CH:8][C:3]=4[O:2][CH3:1])=[CH:15][CH:16]=[CH:17][C:18]=23)[C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of tert-butyl N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (170 mg) dissolved in N,N-dimethylformamide (4 mL) was added sodium hydride (60% in oil; 22 mg) and (bromomethyl)cyclopropane (0.043 mL), and the reaction mixture was stirred for 30 minutes at 40° C. Water was added to the obtained reaction mixture, extraction was performed with ethyl acetate and the organic extract was washed with brine. The obtained organic extract was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure to afford a crude product of tert-butyl N-cyclopropylmethyl-N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate.

Workup

extractionthe organic extract
washwas washed with brine
extractionThe obtained organic extract
dry with materialwas dried over anhydrous magnesium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-99689b494fa440e1b8c5d052a2135f60
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323569B2

Linked notes

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