Dimethyl Sulfoxide → HCID 10279968, compound

HRID 2244207Notes

Reaction equation

HRID 2244207 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](NC)[CH:2]=1.ClC(Cl)(Cl)[C:11]([C:13]1[N:22]2[C:16]([CH2:17][N:18]([C:27]([C:29]3[CH:34]=[CH:33][C:32]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[O:41][CH3:42])=[CH:31][CH:30]=3)=[O:28])[C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[CH2:21]2)=[CH:15][CH:14]=1)=[O:12].[CH2:45]([N:47](CC)CC)C.CS(C)=O>ClCCl.C(#N)C>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:32]1[CH:31]=[CH:30][C:29]([C:27]([N:18]2[C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[CH2:21][N:22]3[C:13]([C:11]([NH:47][CH2:45][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:12])=[CH:14][CH:15]=[C:16]3[CH2:17]2)=[O:28])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 140376N-Methyl-3-pyridinamineHCID 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}ethanone

Product 1

HCID 10279968HCID 10279968, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the procedure of Example 6, Step D, from pyridin-3-yl-methylamine (0.515 mL, 5.057 mmol), 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 (1.30 g, 2.41 mmol), triethylamine (0.738 mL, 5.30 mmol), dimethylsulfoxide (0.854 mL, 12.04 mmol) and acetonitrile (15 mL). The crude material was purified by flash column chromatography on silica gel Merck-60 using 4% methanol in dichloromethane as the eluant to give a light yellow solid. The solid was taken up in dichloromethane and precipitated by the addition of diethyl ether and ethyl acetate. The precipitate was collected by filtration and dried under reduced pressure to give the title compound (0.69 g, 54%) of as a white solid, m.p. 123-127° C.

Workup

  1. customThe title compound was prepared
  2. customThe crude material was purified by flash column chromatography on silica gel
  3. customto give a light yellow solid
  4. customprecipitated by the addition of diethyl ether and ethyl acetate
  5. filtrationThe precipitate was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-fdcca4e9346d43a39b06d6b04e93ab1d
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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