Isopropyl isocyanate → HCID 131718099, compound

HRID 2255545Notes

Reaction equation

HRID 2255545 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])[N:6]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33]([C:34]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=1)[C:5]2=[O:53].[CH:54]([N:57]=[C:58]=[O:59])([CH3:56])[CH3:55]>C(Cl)Cl.CCOC(C)=O>[CH2:12]([C:7]1[N:6]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33]([C:34]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[N:32]=[N:31][N:30]=3)=[CH:21][CH:22]=2)[C:5](=[O:53])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:58](=[O:59])[NH:57][CH:54]([CH3:56])[CH3:55])[CH:3]=2)[N:8]=1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 131718094HCID 131718094, compound

Product 1

HCID 131718099HCID 131718099, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution of 0.069 g (0.1 mmol) of the aminoquinazolinone from Example 40 in 1 mL of CH2Cl2 was added 12.7 mg (0.15 mmol) of isopropylisocyanate. The reaction mixture was stirred for 3 days. The mixture was diluted with 20 mL of EtOAc, washed with water (2×5 mL), brine (1×5 mL) and dried over MgSO4. The mixture was filtered and concentrated in vacuo and the residue was purified by MPLC over a silica Lobar B column eluting with 50% EtOAc/hexanes to give 59.5 mg (0.07 mmol) of an oil, 76% yield. 1H-NMR (CDCl3 300 MHz): 0.86 (t, 3H, J=7.3 Hz), 1.07 (d, 6H, J=6.5 Hz), 1.29 (m, 2H), 1.68 (m, 2H), 2.59 (3 line m, 2H, J=7.06 Hz), 3.95 (m, 1H), 5.18 (d, 1H,J=7.7 Hz), 5.28 (bs, 2H), 7.12 (m, 6H), 7.07 (d, 2H), 7.19-7.32 (m, 11H), 7.43 (m, 2H), 7.57 (m, 2H), 7.90 (m, 2H), 8.13 (m, 1H).

Workup

  1. washwashed with water (2×5 mL), brine (1×5 mL)
  2. dry with materialdried over MgSO4
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by MPLC over a silica Lobar B column
  6. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-7afc62ccf27f49cfbb4d7ff84cf2329c
Source dataset
uspto-grants-1993_08
Patent number
US05240928

Reaction notes

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