Ethyl isocyanate → HCID 18518669, compound

HRID 1369088Notes

Reaction equation

HRID 1369088 reaction equation
[CH2:1]([N:3]([CH2:35][CH3:36])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:19]([F:22])([F:21])[F:20])[CH:11]=[C:12]([C:15]#[C:16][CH2:17][NH2:18])[CH:13]=2)[C:8]([OH:33])([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[C:7]1=[O:34])[CH3:2].C([N:39]=[C:40]=[O:41])C.[CH2:42](N(CC)CC)[CH3:43]>C1COCC1>[CH2:35]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:19]([F:20])([F:22])[F:21])[CH:11]=[C:12]([C:15]#[C:16][CH2:17][N:18]([CH2:42][CH3:43])[C:40]([NH2:39])=[O:41])[CH:13]=2)[C:8]([OH:33])([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)[C:7]1=[O:34])[CH3:36]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 18518580HCID 18518580, compound

Product 1

HCID 18518669HCID 18518669, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-(3-amino-1-propynyl)-3-hydroxy-3-(2-naphthyl)oxindole (40 mg, 0.074 mmol), ethyl isocyanate (0.0065 mL, 0.0821 mmol), and triethylamine (0.025 mL, 0.0821 mmol) in THF (0.5 mL) was stirred for 4 h at room temperature and the reaction was quenched with sat. aqueous NaHCO3. The mixture was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated. The residue was purified by column chromatography with 40:1 to 20:1 chloroform/methanol to give the title compound (20.6 mg). The hydrochloride of the title compound was obtained by treating with 4 N HCl in dioxane followed by concentration to dryness.

Workup

  1. customthe reaction was quenched with sat. aqueous NaHCO3
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography with 40:1 to 20:1 chloroform/methanol

Sources & evidence

ORD record
ord-4f5fb6e0199d4251ab8c84491845f96b
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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