Phenyl isocyanate → HCID 67574818, compound

HRID 1599069Notes

Reaction equation

HRID 1599069 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:39]=[N:40][CH:41]=[CH:42][CH:43]=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:39]=[N:40][CH:41]=[CH:42][CH:43]=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 67574898HCID 67574898, compound

Product 1

HCID 67574818HCID 67574818, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phenyl isocyanate (36.6 mg, 0.295 mmol) in methylene chloride (1 ml) was added to a solution of 2-(3-Amino-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl) acetamide (140 mg, 0.295 mmol) in methylene chloride (1 ml) and the resultant solution stirred at rt for 16 h. The solvent was removed in vacuo and the residue recrystalised from 5% methanol in ethyl acetate to afford the title compound product (49 mg) as a white powder. 1H NMR (300 MHz, CDCl-3). s 8.72 (s, 1H), 8.56 (d, 1H, J=8.0), 7.92 (d, 1H, J=8.0), 6.91-7.43 (m, 16H), 6.43 (d, 1H, J=8.3), 5.43 (d, 1H, J=8.3), 4.95 (sept, 1H, J=6.8), 4.60 (d, 1H, J=11.8), 4.18 (d, 1H, J=11.8), 3.88 (s, 3H), 1.06 (m, 6H). Low resolution MS (FAB) m/e 593 (m+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue recrystalised from 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-ec90dfb52a614d4f8ec152c01908618b
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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