Thionyl Chloride → 10-{[2'-(Methylthio)-1,1'-biphenyl-4-yl]carbonyl}-n-(pyridin-3-ylmethyl)-10,11-dihydro-5h-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2244219Notes

Reaction equation

HRID 2244219 reaction equation
S(Cl)(Cl)=O.[CH3:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([OH:21])=O)=[CH:15][CH:14]=1.CC1C=CC=C(C)C=1C1C=CC(C([N:38]2[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=3[CH2:42][N:41]3[C:49]([C:52]([NH:54][CH2:55][C:56]4[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=4)=[O:53])=[CH:50][CH:51]=[C:40]3[CH2:39]2)=O)=CC=1>N1C=CC=CC=1>[CH3:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19]([N:38]2[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=3[CH2:42][N:41]3[C:49]([C:52]([NH:54][CH2:55][C:56]4[CH:57]=[N:58][CH:59]=[CH:60][CH:61]=4)=[O:53])=[CH:50][CH:51]=[C:40]3[CH2:39]2)=[O:21])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 1595160610-[(2',6'-Dimethyl-1,1'-biphenyl-4-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamideHCID 225963254-(2-Methylthiophenyl)benzoic acid

Product 1

HCID 1595160810-{[2'-(Methylthio)-1,1'-biphenyl-4-yl]carbonyl}-n-(pyridin-3-ylmethyl)-10,11-dihydro-5h-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 20 mL of thionyl chloride was added 0.244 g (0.001 mol) of 2′-(methylthio)-1,1′-biphenyl-4-carboxylic acid of Step A. The solution was heated under reflux for 1 hour. The excess thionyl chloride was removed in a vacuo. To the residue was added 25 mL of dry pyridine and 0.318 g (0.001 mol) of N-(pyridyl-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 12. The reaction was allowed to stand at room temperature for 1 hour and the pyridine was removed in vacuo. The residue was collected and washed with water giving a tan solid (0.62 g), m.p. 172-175° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 1 hour
  3. customThe excess thionyl chloride was removed in a vacuo
  4. customthe pyridine was removed in vacuo
  5. customThe residue was collected
  6. washwashed with water giving a tan solid (0.62 g), m.p. 172-175° C.

Sources & evidence

ORD record
ord-6e1e1f302d9e457d8dd317d25f0fd279
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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