2-Aminothiazole → HCID 44234337, compound

HRID 391273Notes

Reaction equation

HRID 391273 reaction equation
CO[C:3]([CH:5]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:7]=2[C:6]1=[O:17])=[O:4].[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1>C1(C)C(C)=CC=CC=1>[S:20]1[CH:21]=[CH:22][N:23]=[C:19]1[NH:18][C:3]([CH:5]1[CH2:11][CH2:10][O:9][C:8]2[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:7]=2[C:6]1=[O:17])=[O:4]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 66841714HCID 66841714, compound

Product 1

HCID 44234337HCID 44234337, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

8-Fluoro-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid methyl ester (0.6 mmol) and 2-aminothiazol (0.6 mmol) were dissolved in 2.5 ml xylene. Reaction was performed by microwave irradiation for 30 minutes at 140° C. The solution obtained from this reaction was cooled to room temperature and extracted by 2 mol/l hydrochloric acid and ethyl acetate. The ethyl acetate extract was dried over sodiumsulfate and the solvent removed in vacuo. After evaporation of the solvent in vacuo 8-Fluoro-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid thiazol-2-ylamide was obtained as a white powder in a yield of 7%. LC-MS: 1.9 min, 307.0 (MH+) 1H-NMR: (DMSO-d6, 500 MHz): d [ppm]: 12.102 (s, 1H), 7.731 (t, 1H, J=7.3 Hz), 7.464 (d, 1H, J=3.2 Hz), 7.234 (d, 1H, J=3.6 Hz), 7.056 (m, 2H, J=7.8 Hz), 4.654 (m, 1H, J=2.6 Hz), 4.340 (m, 1H, J=7.6 Hz), 4.013 (m, 1H, J=7.2 Hz), 2.502 (m, 2H, J=1.8 Hz)

Workup

  1. customReaction
  2. customwas performed by microwave irradiation for 30 minutes at 140° C
  3. customThe solution obtained from this reaction
  4. extractionextracted by 2 mol/l hydrochloric acid and ethyl acetate
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over sodiumsulfate
  7. customthe solvent removed in vacuo
  8. customAfter evaporation of the solvent in vacuo 8-Fluoro-5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepine-4-carboxylic acid thiazol-2-ylamide
  9. customwas obtained as a white powder in a yield of 7%
  10. custom1.9 min, 307.0 (MH+) 1H-NMR: (DMSO-d6, 500 MHz): d [ppm]: 12.102 (s, 1H), 7.731 (t, 1H, J=7.3 Hz), 7.464 (d, 1H, J=3.2 Hz), 7.234 (d, 1H, J=3.6 Hz), 7.056 (m, 2H, J=7.8 Hz), 4.654 (m, 1H, J=2.6 Hz), 4.340 (m, 1H, J=7.6 Hz), 4.013 (m, 1H, J=7.2 Hz), 2.502 (m, 2H, J=1.8 Hz)

Sources & evidence

ORD record
ord-e0810f31c24649a4af64b8052ba3e8e6
Source dataset
uspto-grants-2013_02
Patent number
US08383838B2

Reaction notes

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