Dimethylformamide dimethyl acetal → 3-{4-[(2E)-3-(dimethylamino)prop-2-enoyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20595Notes

Reaction equation

HRID 20595 reaction equation
[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C@@H:25]([CH3:29])[CH2:26][O:27][CH3:28])[CH:23]=2)[C:12]([NH:14][C:15]2[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=2)=[O:13])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CO[CH:34](OC)[N:35]([CH3:37])[CH3:36]>>[CH3:34][N:35]([CH3:37])/[CH:36]=[CH:2]/[C:1]([C:4]1[CH:31]=[CH:30][C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:21]=[C:22]([O:24][C@@H:25]([CH3:29])[CH2:26][O:27][CH3:28])[CH:23]=2)[C:12]([NH:14][C:15]2[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=2)=[O:13])=[CH:6][CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 593469153-(4-Acetylphenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 593469113-{4-[(2E)-3-(dimethylamino)prop-2-enoyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 83.3%

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(4-acetylphenoxy)-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1′-methyl-1H-pyrazol-3-yl)benzamide (812 mg, 1.92 mmol) and N,N-dimethylformamide dimethyl acetal (10.2 mL, 77 mmol) was heated to 100° C. in a ‘Smith Creator’ microwave for 140 mins. The volatiles were removed under reduced pressure and the resulting oil purified by chromatography on silica, eluting with 0-20% methanol in DCM, to give the desired product (765 mg).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting oil purified by chromatography on silica
  3. washeluting with 0-20% methanol in DCM

Sources & evidence

ORD record
ord-d8a02c3d16a646df9639e69743212fac
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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