Oxalyl chloride → HCID 19379090, compound

HRID 2210553Notes

Reaction equation

HRID 2210553 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:26])[CH2:22][C:23](O)=[O:24])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.N.CC#[N:36]>CN(C=O)C.C1(C)C=CC=CC=1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:26])[CH2:22][C:23]([NH2:36])=[O:24])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 15587892HCID 15587892, compoundHCID 19379070HCID 19379070, compound

Product 1

HCID 19379090HCID 19379090, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

In the same manner as Example, 9, 3-[4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]-3-oxo-propionic acid (0.70 mmol, 0.25 g), oxalyl chloride (0.77 mmol, 0.385 mL; 2M solution in CH2Cl2), DMF (4 drops) and saturated NH3 /CH3CN solution (10 mL) in dry toluene (10 mL) afforded a solid which was triturated in Et2O/hexane to give the title compound as a white solid, mp=132°-133° C. (0.40 mmol, 0.150 g, 60%).

Workup

  1. customwas triturated in Et2O/hexane

Sources & evidence

ORD record
ord-b5d5120c436c4ef4bcf7aa602117f59d
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

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