Dimethyl Sulfoxide → N-(Pyridin-3-ylmethyl)-10-[(2,2',6'-trimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2244211Notes

Reaction equation

HRID 2244211 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].[NH2:38][CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=1.CS(C)=O.C(N(CC)CC)C>C(#N)C>[N:42]1[CH:43]=[CH:44][CH:45]=[C:40]([CH2:39][NH:38][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:41]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 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 15951604N-(Pyridin-3-ylmethyl)-10-[(2,2',6'-trimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamideYield 50.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 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 Step D (0.610 g, 1.1 mmol) and 3-(aminomethyl)pyridine (0.119 g, 1.0 mmol) in acetonitrile (15 mL), was treated with dimethylsulfoxide (0.432 g, 5.5 mmol) and triethylamine (0.246 g, 2.4 mmol). The mixture was heated under nitrogen at 80° C. overnight, and then concentrated. The residue was taken up in dichloromethane (25 mL), washed with brine and water, dried over anhydrous magnesium sulfate and concentrated. Flash chromatography of the residue on silica gel Merck-60 eluting with 85:10:5 ethylacetate:hexane:dichloromethane provided the title compound (0.275 g).

Workup

  1. concentrationconcentrated
  2. washwashed with brine and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluting with 85:10:5 ethylacetate

Sources & evidence

ORD record
ord-1663d07cca4c40aca436d450bbbf7d95
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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