Ethyl isocyanate → [4-(1-Ethylcarbamoyl-piperidin-4-yloxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester

HRID 1929587Notes

Reaction equation

HRID 1929587 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:22])[CH:11]=2)[CH:6]=1.[N:24]([CH2:27][CH3:28])=[C:25]=[O:26]>ClCCl>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]2[CH2:17][CH2:18][N:19]([C:25](=[O:26])[NH:24][CH2:27][CH3:28])[CH2:20][CH2:21]2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:22])[CH:11]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 59326737[6-Fluoro-4-(piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester

Product 1

HCID 59326763[4-(1-Ethylcarbamoyl-piperidin-4-yloxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of [6-fluoro-4-(piperidin-4-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (the intermediate for example 4-1, 1st step, 20 mg, 0.063 mmol) and isocyanato-ethane (0.05 mL) and dichloromethane was stirred at room temperature for 4 hours. The resulting mixture was concentrated in vacuo. The residue was purified by flash column (gradient elution with 0-30% ethyl acetate in petroleum ether) to afford [4-(1-ethylcarbamoyl-piperidin-4-yloxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester (21.0 mg, 85%) as a viscous oil.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customThe residue was purified by flash column (gradient elution with 0-30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-bec221e31b20486396278efa882ba321
Source dataset
uspto-grants-2012_05
Patent number
US08188090B2

Reaction notes

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