Phenyl isocyanate → 2,3,4,5-Tetrahydro-N-(4-methoxyphenyl)-N-(1-methylethyl)-2,4-dioxo-3-[[(phenylamino)carbonyl]amino]-5-(2-pyridinyl)-1H-1,5-benzodiazepine-1-acetamide

HRID 1599065Notes

Reaction equation

HRID 1599065 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH:11]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([N:22]([CH:31]([CH3:33])[CH3:32])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[O:21])[C:15]2[CH:34]=[CH:35][CH:36]=[CH:37][C:14]=2[N:13]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)[C:12]1=[O:44]>C(Cl)Cl>[O:18]=[C:17]1[N:16]([CH2:19][C:20]([N:22]([CH:31]([CH3:33])[CH3:32])[C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[O:21])[C:15]2[CH:34]=[CH:35][CH:36]=[CH:37][C:14]=2[N:13]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][N:39]=2)[C:12](=[O:44])[CH:11]1[NH:10][C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 18929586HCID 18929586, compound

Product 1

HCID 189295682,3,4,5-Tetrahydro-N-(4-methoxyphenyl)-N-(1-methylethyl)-2,4-dioxo-3-[[(phenylamino)carbonyl]amino]-5-(2-pyridinyl)-1H-1,5-benzodiazepine-1-acetamideYield 35.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phenyl isocyanate (25.6 mg) in methylene chloride (1 ml) was added to a solution of 2-(3-Amino-2,4-dioxo-5-pyrdin-2-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide (100 mg) in methylene chloride (1 ml) and the resultant mixture was stirred at rt for 4 h. The solvents were removed in vacuo and the residue was recrystalised from ethyl acetate to afford the title product (44 mg) as an off-white solid. 1H NMR (300 MHz, CDCl3); 1.03 (2×d, J=7 Hz, 6H), 3.81 (s, 3H), 4.17 (d J=16 Hz, 1H), 4.37 (d, J=16 Hz, 1H), 5.0 (sept, J=7.1 Hz, 1H), 5.40 (d, J=6.3 Hz, 1H), 6.40 (d, J=5.3 Hz, 1H), 6.8-7.3 (m, 17H), 7.80 (br, 1H), 8.42 (d, J=3.9 Hz, 1H).Tlc (10% MeOH, CH2Cl2) Rf=0.53. m/z [MH]+ =593.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was recrystalised from ethyl acetate

Sources & evidence

ORD record
ord-260090b9f009448ab96161d0193623a0
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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