Dimethylacetamide → HCID 9905120, compound

HRID 704698Notes

Reaction equation

HRID 704698 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:5][CH:4]=1.CC(N(C)C)=O.[NH:23]1[C:31]2[CH:30]=[CH:29][N:28]=[CH:27][C:26]=2[N:25]=[CH:24]1>>[CH:11]1([CH2:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:28]3[CH:29]=[CH:30][C:31]4=[N:23][CH:24]=[N:25][C:26]4=[CH:27]3)=[CH:4][CH:5]=2)=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 15158212HCID 15158212, compoundHCID 178419860HCID 178419860, compound

Product 1

HCID 9905120HCID 9905120, compoundYield 57%

Conditions

Temperature
115 °C

Procedure

The product of Example G (270 mg, 0.0011 moles) was dissolved in 5 mls of dimethylacetamide containing 135 mg (0.0011 moles) of 1H-imidazo[4,5-c]pyridine and stirred under nitrogen at 80° C. for 24 hours and at 115° C. for an additional 6 hours. The reaction appeared to be complete by TLC. After cooling, the solvent was removed by vacuum distillation. Chromatography of the crude product (twice) on silica gel using CH3OH/CH2Cl2 /NH4OH (5/95/1) as the eluent gave 200 mg (57%) of the title compound as a monohydrate m.p.=153°-156° C.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed by vacuum distillation

Sources & evidence

ORD record
ord-8f9500a8e8ae40fc9a9d9ec477f0d722
Source dataset
uspto-grants-1991_01
Patent number
US04988707

Reaction notes

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