Ethyl isocyanate → HCID 67109704, compound

HRID 2370991Notes

Reaction equation

HRID 2370991 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:18]2[C:19]([CH3:24])=[N:20][O:21][C:22]=2[CH3:23])=[CH:5][CH:4]=1.[N:25]([CH2:28][CH3:29])=[C:26]=[O:27]>CN(C=O)C>[CH3:24][C:19]1[C:18]([C:10]2[N:11]([C:26]([NH:25][CH2:28][CH3:29])=[O:27])[C:12]3[C:17]([C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:22]([CH3:23])[O:21][N:20]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanate2×HCID 67108903HCID 67108903, compound

Product 1

HCID 67109704HCID 67109704, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-(3-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole (15 mg, 0.06 mmol) and isocyanatoethane (40 μl) were mixed 1 ml dry DMF under nitrogen. The mixture was heated at 70° C. for 3 h. 100 μl isocyanatoethane were added and the heating at 70° C. continued over night. The crude reaction mixture was purified by prep HPLC. 8.0 mg 2-(3,5-dimethylisoxazol-4-yl)-N-ethyl-3-(4-methoxyphenyl)-1H-indole-1-carboxamide was obtained.

Workup

  1. waitthe heating at 70° C. continued over night
  2. customThe crude reaction mixture
  3. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-35929eebde0c4247817cc77c81a3a1e0
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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