Hydroxylamine → HCID 178482346, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:16]=[C:15]([C:17]3[N:18]=[C:19]([NH:22][CH3:23])[S:20][CH:21]=3)[O:14][N:13]=2)=O)[CH:5]=[CH:6][C:7]=1[F:8].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:30][OH:31]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:16]=[C:15]([C:17]3[N:18]=[C:19]([NH:22][CH3:23])[S:20][CH:21]=3)[O:14][N:13]=2)=[N:30][OH:31])[CH:5]=[CH:6][C:7]=1[F:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
N-(3-Chloro-4-fluorophenyl)-5-[2-(methylamino)-1,3-thiazol-4-yl]isoxazole-3-carboxamide (22 mg, 0.062 mmol) was suspended in benzene (1.5 mL) and phosphorus pentachloride (33 mg, 0.16 mmol) was added. The mixture was stirred for 3 h at 80° C. and evaporated in vacuo to give a tan solid. Benzene (2.0 mL) was added and the mixture was reevaporated twice. The solid was dissolved in tetrahydrofuran (1.5 mL) and 20 M aqueous hydroxylamine (70 μL, 1.0 mmol) was added and the mixture was stirred for 2 h. The mixture was evaporated in vacuo and triturated with methanol to give a white precipitate which was filtered and washed with methanol to give the desired product (12 mg, 35%). MF=C14H11ClFN5O2S; LCMS calculated for C14H11ClFN5O2S; (M+H)+: m/z=368. 1H NMR (400 MHz, DMSO-d6) δ: 11.20 (s, 1H), 8.75 (s, 1H), 7.82 (m, 1H), 7.32 (s, 1H), 7.20 (m, 1H), 6.92 (m, 1H), 6.65 (m, 1H), 2.82 (m, 3H).
Workup
- customevaporated in vacuo
- customto give a tan solid
- customthe mixture was reevaporated twice
- dissolutionThe solid was dissolved in tetrahydrofuran (1.5 mL)
- stirringthe mixture was stirred for 2 h
- customThe mixture was evaporated in vacuo
- customtriturated with methanol
- customto give a white precipitate which
- filtrationwas filtered
- washwashed with methanol
Sources & evidence
- ORD record
- ord-b4a41ae8e0ed49e49600997383cae4db
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377976B2
Reaction notes
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