Pyridine → Benzyl 4-[5-(diethoxymethyl)-1-methyl-1H-pyrazol-3-yl]phenylcarbamate

HRID 456793Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:18][CH2:19][CH3:20])[C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[CH:6]=1)[CH3:2].N1C=CC=CC=1.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>ClCCl>[CH2:19]([O:18][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[N:9]([CH3:10])[N:8]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]([NH:15][C:28](=[O:29])[O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:16][CH:17]=2)[CH:6]=1)[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

4-[5-(Diethoxymethyl)-1-methyl-1H-pyrazol-3-yl]aniline (Intermediate 10, 5.9 g, 21.5 mmol), and pyridine (4 ml, 50 mmol) were dissolved in dichloromethane (25 ml) at 0° C. Benzyl chloroformate (3.8 ml, 26.7 mmol) was added slowly over 5 minutes and the resulting mixture was stirred at 0° C. for 30 min. The mixture was diluted with dichloromethane and washed with 1M HCl, saturated NaCl, then dried over sodium sulfate and evaporated give the title compound as a thick light orange oil (9.6 g).

Workup

washwashed with 1M HCl, saturated NaCl
dry with materialdried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-e8c08db061024efb885fb567580e9fd0
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186738B2

Reaction notes

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