Phenyl isocyanate → HCID 19063689, compound

HRID 482355Notes

Reaction equation

HRID 482355 reaction equation
[NH2:1][CH:2]1[N:11]2[C:7](=[N:8][N:9]=[CH:10]2)[C:6]2[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=2[N:4]([CH2:16][C:17]([N:19]([CH:26]([CH3:28])[CH3:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:18])[C:3]1=[O:29].[C:30]1([N:36]=[C:37]=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[CH:26]([N:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:17](=[O:18])[CH2:16][N:4]1[C:3](=[O:29])[CH:2]([NH:1][C:37]([NH:36][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:38])[N:11]2[C:7](=[N:8][N:9]=[CH:10]2)[C:6]2[CH:12]=[CH:13][CH:14]=[CH:15][C:5]1=2)([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 19063678HCID 19063678, compound

Product 1

HCID 19063689HCID 19063689, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-Amino-5-oxo-4,5-dihydro-1,2,3a,6-tetraaza-benzo[e]azulen-6-yl)-N-isopropyl-N-phenyl-acetamide (140 mg, 0.361 mmol), prepared as in Intermediate 36, and phenyl isocyanate (39.2 uL, 0.361 mmol) in 5 mL dry DCM is stirred at ambient temperature under nitrogen overnight. After concentrating in vacuo, the residue is chromatographed on flash grade silica gel using 95% ethyl acetate in n-hexane. The fractions containing the product are combined, concentrated in vacuo, and triturated with hexane. After removing the solvent in vacuo, the product is dried overnight at ambient temperature under high vacuum to provide the title compound (84 mg, 0.165 mmol) as a white solid. The product is lyophilized from acetonitrile/water. 1H NMR (300 MHz, d6-DMSO): 0.89-0.96 (m, 6H); 4.02 (d, J=16.3 Hz, 1H); 4.16 (d, J=16.3 Hz, 1H); 4.62-6.73 (m, 1H); 5.99-6.05 (m, 1 H); 6.93 (t, J=7.2 Hz; 1H); 7.10-7.89 (m, 14H); 8.10 (s, 1H); 9.30 (s, 1H). MS (FAB): [M+H]+ 510.

Workup

  1. concentrationAfter concentrating in vacuo
  2. customthe residue is chromatographed on flash grade silica gel using 95% ethyl acetate in n-hexane
  3. additionThe fractions containing the product
  4. concentrationconcentrated in vacuo
  5. customtriturated with hexane
  6. customAfter removing the solvent in vacuo
  7. customthe product is dried overnight at ambient temperature under high vacuum

Sources & evidence

ORD record
ord-85b8bf6395d7426eb77994264c924a41
Source dataset
uspto-grants-1998_08
Patent number
US05795887

Reaction notes

Loading…