Phenyl isocyanate → HCID 10230873, compound

HRID 1270187Notes

Reaction equation

HRID 1270187 reaction equation
[CH:1]1([C:7]2[CH:32]=[CH:31][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:24]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:33]1([N:39]=[C:40]=[O:41])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[CH:1]1([C:7]2[CH:32]=[CH:31][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:24]([C:27]([NH:29][NH:30][C:40]([NH:39][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[O:41])=[O:28])=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 10113410HCID 10113410, compound

Product 1

HCID 10230873HCID 10230873, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10-(4-cyclohexyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-carboxylic acid hydrazide of Example 8 (0.56 g) and phenylisocyanate (0.17 g) in tetrahydrofuran (25 mL) was refluxed under stirring for four hours. After removal of all volatiles at reduced pressure, the residue was treated with water and extracted with dichloromethane. The combined extracts were dried over anhydrous sodium sulfate and the solution filtered through a short column of Magnesol®. After elution with several additional volumes of dichloromethane, the combined eluate was evaporated to dryness to provide the title compound as a yellow amorphous solid (0.18 g).

Workup

  1. temperaturewas refluxed
  2. customAfter removal of all volatiles at reduced pressure
  3. additionthe residue was treated with water
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  6. filtrationthe solution filtered through a short column of Magnesol®
  7. washAfter elution with several additional volumes of dichloromethane
  8. customthe combined eluate was evaporated to dryness

Sources & evidence

ORD record
ord-7993060ca6a34f7e96801f1e66289a82
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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