Water → HCID 53994067, compound

HRID 442670Notes

Reaction equation

[CH2:1]1[O:21][C:4]2=[CH:5][C:6]3[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][NH:10][C:9](=[O:19])[CH2:8][C:7]=3[CH:20]=[C:3]2[O:2]1.C(N(CC)CC)C.[CH3:29][N:30]=[C:31]=[O:32].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]1[O:21][C:4]2=[CH:5][C:6]3[C:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][N:10]([C:31]([NH:30][CH3:29])=[O:32])[C:9](=[O:19])[CH2:8][C:7]=3[CH:20]=[C:3]2[O:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 7,8-methylenedioxy-1-phenyl-3,5-dihydro-2,3-benzodiazepin-4(4H)-one (130 mg, 0.46 mmol) in CH2Cl2 (5 ml) was added triethylamine (1 mL), DMAP (5 mg) and methylisocyanate (60 mg) and the mixture was stirred at 25° C. for 24 h. The reaction mixture was then poured into a separatory funnel containing water (50 mL) and the product was extracted with CH2Cl2 (3×40 mL). The combined extracts were dried over Na2SO4 and solvent removed in vacuo. Purification of the residue by chromatography (1:1 of ethyl acetate: hexane) resulted in the product as a white solid (92 mg, 59%), mp, 180°-182.5° C. 1H NMR (CDCl3) 8.60 (bs, 1H), 7.74 (m, 2H), 7.46 (m, 3H), 6.88 (s, 1H), 6.67 (s, 1H), 6.07 (bs, 1H), 6.03 (bs, 1H), 3.54 (s, 1H) 3.54 (s, 1H), 2.93 (s, 1.5H), 2.92 (s, 1.5H).

Workup

additionThe reaction mixture was then poured into a separatory funnel
extractionthe product was extracted with CH2Cl2 (3×40 mL)
dry with materialThe combined extracts were dried over Na2SO4 and solvent
customremoved in vacuo
customPurification of the residue by chromatography (1:1 of ethyl acetate: hexane)

Sources & evidence

ORD record: ord-1107249c922348afbc4ba38153966e1c
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05891871

Reaction notes

Loading…