Dimethyl Sulfoxide → HCID 11998030, compound

HRID 2246839Notes

Reaction equation

HRID 2246839 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])=[CH:23][CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[CH3:37][C:38]1[O:42][N:41]=[C:40]([C:43](CN)=O)[CH:39]=1.CS(C)=O.C([N:53](CC)CC)C>C(#N)C>[CH3:34][O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:25]=[CH:26][C:21]([C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:53][CH2:43][C:40]4[CH:39]=[C:38]([CH3:37])[O:42][N:41]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:20])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 160384072,2,2-trichloro-1-{10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanoneHCID 55289657HCID 55289657, compound

Product 1

HCID 11998030HCID 11998030, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared according to the procedure of Example 2 starting from 2,2,2-trichloro-1-{10-[(2′-methoxy-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 1 (1.483 g, 2.75 mmole), (5-methyl-3-isoxazoyl)methylamine (0.256 g 1.0 eq), dimethylsulfoxide (5.0 eq, 0.896 g, 11.45 mmole), and triethylamine (2.2 eq, 0.510 g, 5 mmole) in 20 mL of acetonitrile. The residue was absorbed on silica gel Merck-60 and flash chromatographed using a gradient from 0 to 20% of ethyl acetate in dichloromethane, to provide a foam (0.460 g) which yielded an off-white solid upon treatment with ethyl acetate/hexane, m.p. 111-113° C.

Workup

  1. customThe residue was absorbed on silica gel Merck-60 and flash
  2. customchromatographed

Sources & evidence

ORD record
ord-2970b28728e04369ab6ae0e2a9851b2f
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

Loading…