m-Tolyl isocyanate → HCID 44213301, compound

HRID 963514Notes

Reaction equation

HRID 963514 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]([N:23]2[CH2:28][CH2:27][S:26][CH2:25][CH2:24]2)=[O:22])[C:3]1=[O:29].[CH3:30][C:31]1[CH:32]=[C:33]([N:37]=[C:38]=[O:39])[CH:34]=[CH:35][CH:36]=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]([N:23]2[CH2:24][CH2:25][S:26][CH2:27][CH2:28]2)=[O:22])[C:3](=[O:29])[CH:2]([NH:1][C:38]([NH:37][C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([CH3:30])[CH:32]=2)=[O:39])[N:8]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 19081141HCID 19081141, compound

Product 1

HCID 44213301HCID 44213301, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3RS)-3-amino-2,3-dihydro-5-(2-fluorophenyl)-1-(thiomorpholin-4-yl)carbonylmethyl-1H-1,4-benzodiazepin-2-one (0.11 g) in dry methylene chloride (10 ml) was added dropwise a solution of 3-methylphenyl isocyanate (0.043 g) in dry methylene chloride (5 ml) at ambient temperature. After completion of addition, the mixture was stirred at the same condition overnight. The reaction mixture was concentrated in vacuo to afford a crude product. The product was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and methanol (100:1) to afford N-[(3RS)-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1-(thiomorpholin-4-yl) carbonylmethyl-1H-1,4-benzodiazepin-3-yl)-N'-(3-methylphenyl)urea as a colorless crystalline solid (0.10 g).

Workup

  1. additionAfter completion of addition
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto afford a crude product
  4. customThe product was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and methanol (100:1)

Sources & evidence

ORD record
ord-5047c0ce41694c48a7c21f0e916a209c
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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