Sodium Bicarbonate → HCID 74020192, compound

HRID 242548Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of the product of step 1 (1.1 g) in ethanol (11 ml) was added thiourea (193 mg) at room temperature, and the mixture stirred at 70° C. for 30 minutes. The reaction mixture was cooled to room temperature and poured into saturated aqueous sodiumbicarbonate. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate to give 7-(2-aminothiazol-4-yl)-5-(3-bromopropylidene)-5,11-dihydro[1]benzoxepino[2,3-b]pyridine (749 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe aqueous layer was extracted with ethyl acetate
washthe organic layer was washed with saturated aqueous sodium chloride
dry with materialdried with magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-367079cadff24b3797609bd21c7a6b70
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653096B2

Reaction notes

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