Ethanol → HCID 29945563, compound

HRID 532430Notes

Reaction equation

HRID 532430 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]([C:20]2[S:21][C:22]([Br:26])=[CH:23][C:24]=2[NH2:25])=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[CH2:27](O)C>>[Br:26][C:22]1[S:21][C:20]2[C:18](=[O:19])[N:17]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][N:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:27]=[N:25][C:24]=2[CH:23]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 29945558HCID 29945558, compound

Product 1

HCID 29945563HCID 29945563, compound

Procedure

A solution of 3-amino-5-bromothiophene-2-carboxylic acid [3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]amide (415 mg) was heated in ethyl o-formate (12.4 mL) at 105° C. overnight; the ethanol produced was distilled off. The reaction solution was then mixed with ethyl acetate and water. The aqueous phase was extracted several times with ethyl acetate, and then the combined organic phases were dried over sodium sulfate and concentrated. The product with the molecular weight of 450.36 (C19H20BrN3O3S) was obtained in this way; MS (ESI): 451, 453 (M+H+).

Workup

  1. distillationwas distilled off
  2. additionThe reaction solution was then mixed with ethyl acetate and water
  3. extractionThe aqueous phase was extracted several times with ethyl acetate
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product with the molecular weight of 450.36 (C19H20BrN3O3S) was obtained in this way

Sources & evidence

ORD record
ord-26f86dd46db6490c9b6753e3522ecbdb
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

Loading…