Methyl Isocyanate → HCID 22462773, compound

HRID 1937189Notes

Reaction equation

HRID 1937189 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:13]([O:23][CH3:24])[CH:12]=3)=[C:8]([C:25]3[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=3)[S:7][C:6]=2[CH:32]=1.C(=O)(O)[O-].[Na+].[CH3:38][N:39]=[C:40]=[O:41]>C1COCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([CH2:17][N:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)=[C:13]([O:23][CH3:24])[CH:12]=3)=[C:8]([C:25]3[CH:26]=[CH:27][C:28]([NH:31][C:40]([NH:39][CH3:38])=[O:41])=[CH:29][CH:30]=3)[S:7][C:6]=2[CH:32]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 516892Sodium BicarbonateHCID 22462791HCID 22462791, compound

Product 1

HCID 22462773HCID 22462773, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Hydroxy-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]-2-[4-aminophenyl]benzo[b]thiophene (80 mg) was dissolved in THF (5.0 mL), treated with sodium bicarbonate (45 mg) while stirring at ambient temperature, cooled to 0° C. in an ice bath before treated with methyl isocyanate (42 μL) under argon. The reaction mixture. was stirred at ambient temperature for 24 h and concentrated. Chromatography with Et3N:MeOH:EtOAc (5:10:85) afforded the title compound (50 mg).

Workup

  1. temperaturecooled to 0° C. in an ice bath
  2. stirringwas stirred at ambient temperature for 24 h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-049dae2b8b9e4be4b0ac0352ff1ef447
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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