Dimethyl Sulfoxide → 10-[(2,2'-Dimethyl-1,1'-biphenyl-4-yl)carbonyl]-N-{[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2246848Notes

Reaction equation

HRID 2246848 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].CS(C)=O.[CH3:41][O:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[O:53][N:52]=[C:51]([CH2:54][NH2:55])[N:50]=2)=[CH:45][CH:44]=1>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:55][CH2:54][C:51]4[N:50]=[C:49]([C:46]5[CH:45]=[CH:44][C:43]([O:42][CH3:41])=[CH:48][CH:47]=5)[O:53][N:52]=4)=[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 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}ethanoneHCID 17604973[5-(4-Methoxyphenyl)-1,2,4-oxadiazol-3-yl]methanamine

Product 1

HCID 1199985110-[(2,2'-Dimethyl-1,1'-biphenyl-4-yl)carbonyl]-N-{[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A mixture 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 9 (0.26 mmol), dimethylsulfoxide (100 uL) and [5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methylamine of Step A (0.546 mmol) in acetonitrile (2.5 mL) was heated to 85° C. for 16 hours. After cooling the solvent was evaporated and the residue was taken up in dichloromethane (10 mL). This was washed with water (2×), dried over anhydrous sodium sulfate, and evaporated. The residue was purified by HPLC (Normal phase, Luna CN bonded packing) and crystallized from ethyl acetate/hexane, m.p. 133-135° C.

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated
  3. washThis was washed with water (2×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was purified by HPLC (Normal phase, Luna CN bonded packing)
  7. customcrystallized from ethyl acetate/hexane, m.p. 133-135° C.

Sources & evidence

ORD record
ord-98d24e96edd243359735d1fab3f5b4e1
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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