Ethyl isocyanate → HCID 59000772, compound

HRID 1594015Notes

Reaction equation

HRID 1594015 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[CH2:6]([O:8][C:9]([C:11]1[C:12]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:13]([CH2:32][CH2:33][CH2:34][OH:35])[N:14]2[C:19]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][C:16]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)=[N:15]2)=[O:10])[CH3:7]>C(N(C(C)C)CC)(C)C.CC#N>[CH2:6]([O:8][C:9]([C:11]1[C:12]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:13]([CH2:32][CH2:33][CH2:34][O:35][C:4](=[O:5])[NH:3][CH2:1][CH3:2])[N:14]2[C:19]=1[C:18]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[CH:17][C:16]([N:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1)=[N:15]2)=[O:10])[CH3:7]

Participants

5

Reactant 2

HCID 8022Ethyl isocyanateHCID 52943384HCID 52943384, compound

Product 1

HCID 59000772HCID 59000772, compound

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl isocyanate (50 μL, 0.063 mmol) and diisopropylethyl amine (1 drop) were added to a solution of 41 (30 mg, 0.062 mmol) in CH3CN (10 mL). The reaction mixture was heated at 50° C. for 18 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel, 35% EtOAc/hexane) to provide the title compound as a white solid. 1H NMR (DMSO-d6) δ 0.89 (t, J=7.1 Hz, 3H), 0.99 (t, J=7.2 Hz, 3H), 1.20 (t, J=7.1 Hz, 3H), 1.91 (m, 2H), 2.96 (m, 2H), 3.22 (m, 2H), 3.53 (m, 6H), 3.71 (m, 4H), 3.96 (m, 2H), 4.19 (q, J=7.1 Hz, 2H), 6.78 (s, 1H), 7.00 (m, 1H), 7.41 (m, 2H), 7.46 (m, 3H). Mass Spectrum (ESI+) m/e=553.2 (M+H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (silica gel, 35% EtOAc/hexane)

Sources & evidence

ORD record
ord-cf566a6d1a18424f817316d8643434c4
Source dataset
uspto-grants-2007_11
Patent number
US07300932B2

Reaction notes

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