Phosphorus oxide (P4O10) → HCID 59003108, compound

HRID 2353988Notes

Reaction equation

[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=O)[CH2:19][C:20](=O)[CH3:21])[C:13]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:12]1=2)[C:8](=[O:10])[CH3:9].O.[NH2:39][NH2:40].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>CO.O>[F:36][C:2]([F:37])([F:1])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]2[CH:19]=[C:20]([CH3:21])[NH:40][N:39]=2)[C:13]2[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:12]1=2)[C:8](=[O:10])[CH3:9]

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of N-(3,5-Bis-trifluoromethyl-benzyl)-N-[8-chloro-1-(3-oxo-butyryl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-acetamide (0.13 mmol, 72 mg), hydrazine hydrate (1.3 mmol, 40.0 μL) in MeOH (2 mL) was added P4O10 (0.5 g) at room temperature. The resulting suspension was stirred vigorously at 70° C. for 12 h. After completion, the mixture was diluted with water (20 mL), and extracted with EtOAc (3×20 mL). The combined organic layers were washed with water and brine, dried over Na2SO4 and evaporated to dryness. Flash chromatography (EtOAc-Hexane as eluent 1:1) afforded the title compound as viscous foam; Rf 0.28 (EtOAc-Hexane, 1:1, v/v); MS (ES+): 545 (M+H+).

Workup

extractionextracted with EtOAc (3×20 mL)
washThe combined organic layers were washed with water and brine
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-d3c84ccb6b2a43359d290b26badacad7
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749992B2

Reaction notes

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