Phenacylamine → HCID 57896683, compound

HRID 2421907Notes

Reaction equation

HRID 2421907 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][O:15][C:14]3[N:18]=[CH:19][C:20]([C:22](Cl)=[O:23])=[CH:21][C:13]2=3)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30].CCN(C(C)C)C(C)C>C1COCC1.CCOC(C)=O>[O:30]=[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:28][NH:27][C:22]([C:20]1[CH:19]=[N:18][C:14]2[O:15][CH2:16][CH2:17][N:12]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:26])([F:25])[F:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[C:13]=2[CH:21]=1)=[O:23]

Participants

6

Reactant 3

HCID 11952PhenacylamineHCID 81531DiisopropylethylamineHCID 86634654HCID 86634654, compound

Product 1

HCID 57896683HCID 57896683, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonyl chloride (100 mg, 0.246 mmol), in THF (5 mL) was added 2-amino-1-phenylethanone (34.9 mg, 0.258 mmol), and DIPEA (0.086 mL, 0.492 mmol). The reaction was stirred for 2 hours at room temperature. The reaction mixture was diluted with EtOAc (10 mL) and washed with saturated aqueous NaHCO3 (5 mL). The aqueous layer was back extracted with EtOAc (2×5 mL). Combined the organic layers were dried over Na2SO4, filtered and concentrated in vacuo to provide N-(2-oxo-2-phenylethyl)-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxamide (115 mg, 0.246 mmol, 93%) as a light brown oil. The material was used without further purification. LCMS (+ESI) m/z=506.1 [M+H]+.

Workup

  1. washwashed with saturated aqueous NaHCO3 (5 mL)
  2. extractionThe aqueous layer was back extracted with EtOAc (2×5 mL)
  3. dry with materialwere dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9d4b9ca43b94df1836226459ba263ec
Source dataset
uspto-grants-2011_06
Patent number
US07960377B2

Reaction notes

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