Dimethyl Sulfoxide → HCID 10142381, compound

HRID 2244229Notes

Reaction equation

HRID 2244229 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[CH3:33])=[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].[NH2:36][CH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1.CS(C)=O>C(#N)C>[CH3:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][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:36][CH2:37][C:38]4[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=4)=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:20])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 310183-PyridinemethanamineHCID 68688408HCID 68688408, compound

Product 1

HCID 10142381HCID 10142381, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,2,2-trichloro-1-{10-[(2′-methyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-yl}ethanone (1.72 mmol), and 3-aminomethylpyridine (3.44 mmol) in dimethylsulfoxide (8.6 mmol) and acetonitrile (15 mL) was stirred at 80° C. for 18 hours. The solvent was evaporated and the residue dissolved in dichloromethane, washed with water, dried over anhydrous sodium sulfate, and evaporated. The material was purified by HPLC (Normal phase, Luna CN bonded packing) and crystallized from ethyl acetate/hexane. (0.68 g; 77%), m.p. 176-177° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe material was purified by HPLC (Normal phase, Luna CN bonded packing)
  7. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-de4a4a352cce4c938fcbbf5ca1e4f93f
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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