m-Tolyl isocyanate → HCID 19081346, compound

HRID 963515Notes

Reaction equation

HRID 963515 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:3]1=[O:27].[CH3:28][C:29]1[CH:30]=[C:31]([N:35]=[C:36]=[O:37])[CH:32]=[CH:33][CH:34]=1>C(Cl)Cl>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[N:4]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:3](=[O:27])[CH:2]([NH:1][C:36]([NH:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([CH3:28])[CH:30]=2)=[O:37])[N:8]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19081207HCID 19081207, compound

Product 1

HCID 19081346HCID 19081346, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3RS)-3-amino-2,3-dihydro-5-(2-fluorophenyl)-1-(pyridin-3-yl)methyl-1H-1,4-benzodiazepin-2-one (0.48 g) in dry methylene chloride (30 ml) was added dropwise a solution of 3-methylphenyl isocyanate (0.195 g) in dry methylene chloride (5 ml) under nitrogen atmosphere at cooling in an ice-bath. The mixture was stirred under the same temperature for 1 hour and at ambient temperature overnight. The resultant precipitates were collected by filtration and washed with isopropyl ether to afford N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1-(pyridin-3-yl)methyl-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea.

Workup

  1. temperatureat cooling in an ice-bath
  2. customThe resultant precipitates
  3. filtrationwere collected by filtration
  4. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-832c71f6d0364a7aa6ee9f280b91ccd6
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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