Sodium Carbonate → HCID 178513384, compound

HRID 2421903Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[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]#[N:23])=[CH:21][C:13]2=3)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[NH2:27][OH:28].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[OH: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:25])([F:24])[F:1])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[C:13]=2[CH:21]=1)=[NH:23]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonitrile (75 mg, 0.203 mmol) in ethanol (2 mL) and water (0.5 mL) was added hydroxylamine hydrochloride (42.3 mg, 0.609 mmol) and sodium carbonate (108 mg, 1.015 mmol). The reaction was heated to 80° C. and stirred at that temperature for 16 h. The reaction mixture was concentrated in vacuo. The resulting paste was suspended in water (10 mL) and extracted with EtOAc (2×20 mL). The combined organics were dried over anhydrous Na2SO4 and concentrated in vacuo to provide N-hydroxy-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboximidamide (80 mg, 0.199 mmol, 98% yield) as a white solid, which was used without further purification. LCMS (+ESI) m/z=403.1 [M+H]+.

Workup

concentrationThe reaction mixture was concentrated in vacuo
extractionextracted with EtOAc (2×20 mL)
dry with materialThe combined organics were dried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bc7772bc0eaf4fae813e1a1da198cd65
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960377B2

Reaction notes

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