m-Tolyl isocyanate → HCID 19081124, compound

HRID 963519Notes

Reaction equation

HRID 963519 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([N:22]2[CH2:28][CH:27]3[CH2:29][CH2:30][CH:24]([CH2:25][CH2:26]3)[CH2:23]2)=[O:21])[C:3]1=[O:31].[C:32]1([CH3:41])[CH:37]=[CH:36][CH:35]=[C:34]([N:38]=[C:39]=[O:40])[CH:33]=1>ClCCl>[CH:24]12[CH2:25][CH2:26][CH:27]([CH2:29][CH2:30]1)[CH2:28][N:22]([C:20]([CH2:19][N:4]1[C:5]3[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=3[C:7]([CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:8][CH:2]([NH:1][C:39]([NH:38][C:34]3[CH:35]=[CH:36][CH:37]=[C:32]([CH3:41])[CH:33]=3)=[O:40])[C:3]1=[O:31])=[O:21])[CH2:23]2

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19081173HCID 19081173, compound

Product 1

HCID 19081124HCID 19081124, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3RS)-3-amino-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-5-cyclohexyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one (0.19 g) in dichloromethane (10 ml) was added m-tolyl isocyanate (0.064 g) at room temperature. The mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated in vacuo. The residue was subjected by column chromatography on silica gel with chloroform and a mixture of chloroform and ethyl acetate (5:1) to give N-[(3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-5-cyclohexyl-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea (0.075 g) as a white amorphous mass.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiona mixture of chloroform and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-a9206f8969084226867888ce8505258f
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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