Dimethyl Sulfoxide → HCID 16038539, compound

HRID 639212Notes

Reaction equation

HRID 639212 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])=[C:23]([CH3:34])[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][CH:38]([NH2:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.CS(C)=O>C(#N)C>[CH3:34][C:23]1[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:45][CH:38]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[CH3:37])=[O:4])=[CH:6][CH:7]=[C:8]3[CH2:9]2)=[O:20])[CH:26]=[CH:25][C:24]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 74081-PhenethylamineHCID 160384712,2,2-Trichloro-1-{10-[(2,2'-dimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 16038539HCID 16038539, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,2,2-trichloro-1-{10-[(2,2′-dimethyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 6 (2 mmol), α-methylbenzylamine (4.2 mmol) in dimethylsulfoxide (7 mmol) and acetonitrile (15 mL) was stirred at 80° C. for 18 hours. The solvents were evaporated and the residue was dissolved in dichloromethane, washed with water, dried over anhydrous sodium sulfate and evaporated. The compound was purified by HPLC (normal phase, Luna® CN bonded packing (Phenomenex, Torrance, Calif.)) and crystallized from ethyl acetate/hexane. (0.93 g), m.p. 118-124°C. MS [(+)ESI, m/z]: 538 [M+H]+Anal. Calcd for C36H33N2O2: C, 80.12; H, 6.16; N, 7.79. Found: C, 79.97; H, 6.27; N, 7.78.

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe compound was purified by HPLC (normal phase, Luna® CN bonded packing (Phenomenex, Torrance, Calif.))
  7. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-e8047b4ac5d84d8e8229f277b9836bd7
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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