m-Tolyl isocyanate → HCID 10768167, compound

HRID 1596378Notes

Reaction equation

HRID 1596378 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([CH2:9][CH3:10])[C:6]2[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:5]=2[N:4]([CH2:16][C:17]([N:19]2[CH2:25][CH:24]3[CH2:26][CH2:27][CH:21]([CH2:22][CH2:23]3)[CH2:20]2)=[O:18])[C:3]1=[O:28].[CH3:29][C:30]1[CH:31]=[C:32]([N:36]=[C:37]=[O:38])[CH:33]=[CH:34][CH:35]=1>O1CCCC1>[CH:21]12[CH2:22][CH2:23][CH:24]([CH2:26][CH2:27]1)[CH2:25][N:19]([C:17]([CH2:16][N:4]1[C:5]3[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:6]=3[C:7]([CH2:9][CH3:10])=[N:8][CH:2]([NH:1][C:37]([NH:36][C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([CH3:29])[CH:31]=3)=[O:38])[C:3]1=[O:28])=[O:18])[CH2:20]2

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 10500121HCID 10500121, compound

Product 1

HCID 10768167HCID 10768167, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3RS)-3-amino-1-[(3-azabicyclo[3.2.2]non-3-yl)-carbonylmethyl]-2,3-dihydro-5-ethyl-9-methyl-1H-1,4-benzodiazepin-2-one (310 mg) and 3-methylphenyl isocyanate (113 mg) in tetrahydrofuran (8 ml) was stirred at room temperature for 1 hour. The reaction mixture was evaporated in vacuo to dryness. The residue was triturated in diisopropyl ether and collected by filtration to afford N-[(3RS)-1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl 2,3-dihydro-5-ethyl-9-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-(3-methylphenyl)urea (360 mg, 86.2% yield) as a crystalline powder.

Workup

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. customThe residue was triturated in diisopropyl ether
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f96a366dfdba4313a972513d617b4ebb
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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