Dimethyl Sulfoxide → HCID 11998031, compound

HRID 2246838Notes

Reaction equation

HRID 2246838 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[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:34])=[C:23]([CH3:35])[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].[CH3:38][C:39]1[O:43][N:42]=[C:41]([CH2:44][NH2:45])[CH:40]=1.CS(C)=O.C(N(CC)CC)C>C(#N)C>[CH3:38][C:39]1[O:43][N:42]=[C:41]([CH2:44][NH:45][C:3]([C:5]2[N:14]3[C:8]([CH2:9][N:10]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[C:28]([CH3:34])=[CH:29][CH:30]=[CH:31][C:32]=5[CH3:33])=[C:23]([CH3:35])[CH:22]=4)=[O:20])[C:11]4[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=4[CH2:13]3)=[CH:7][CH:6]=2)=[O:4])[CH:40]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 27763061-(5-Methyl-1,2-oxazol-3-yl)methanamineHCID 686871492,2,2-trichloro-1-{10-[(2,2',6'-trimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 11998031HCID 11998031, 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-[(2,2′,6′-trimethyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 3 (1.8 g, 3.26 mmole), (5-methyl-3-isoxazolyl)methylamine (0.305 g, 2.7 mmole), dimethylsulfoxide (1.06 g, 13.6 mmole), and triethylamine (0.605 g, 6 mmole) in 20 mL of acetonitrile. The residue was flash chromatographed on silica Merck-60 using a gradient from 0 to 35% of ethyl acetate in dichloromethane, to provide an orange-yellow foam. Recrystallization from ethyl acetate/dichloromethane/hexane gave a white powder (0.334 g), m.p. 233-234° C.

Workup

  1. customchromatographed on silica Merck-60
  2. customto provide an orange-yellow foam
  3. customRecrystallization from ethyl acetate/dichloromethane/hexane

Sources & evidence

ORD record
ord-42f29be9eb234ca8a63ef032b47f1747
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

Loading…