Oxalyl chloride → HCID 86654678, compound

HRID 880519Notes

Reaction equation

HRID 880519 reaction equation
[C:1](Cl)(=[O:5])[C:2]([Cl:4])=[O:3].[CH3:7][O:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[C:12]1[CH3:22]>C(Cl)(Cl)Cl>[CH3:7][O:8][CH2:9][CH2:10][N:11]1[C:12]([CH3:22])=[CH:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:15]1[C:1](=[O:5])[C:2]([Cl:4])=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chloride2×HCID 66914904HCID 66914904, compound

Product 1

HCID 86654678HCID 86654678, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Oxalyl chloride (0.19 g, 1.53 mmol) was added to a solution of 1-(2-methoxy-ethyl)-2-methyl-4-phenyl-1H-pyrrole (0.30 g, 1.39 mmol) in chloroform (5 mL) at 0° C. and slowly warmed the ambient temperature to RT over 30 min. Completion of reaction and removal of excess oxalyl chloride in vacuo afforded the intermediate acid chloride, [1-(2-methoxy-ethyl)-5-methyl-3-phenyl-1H-pyrrol-2-yl]-oxo-acetyl chloride which was taken in chloroform (5 mL). This was then added to a solution of 3-fluoro-4-morpholin-4-yl-phenylamine (0.19 g, 0.97 mmol) in chloroform (5 mL) with triethyl amine (0.28 g, 2.78 mmol). The reaction was stirred for 30 min at ambient temperature and then diluted with water and extracted into chloroform. Combined organic extracts were washed with saturated bicarbonate solution, dried over anhydrous sodium sulfate and stirred over neutral alumina for 10 min. The mixture was filtered and concentrated in vacuo to afford N-(3-fluoro-4-morpholin-4-yl-phenyl)-2-[1-(2-methoxy-ethyl)-5-methyl-3-phenyl-1H-pyrrol-2-yl]-2-oxo-acetamide (0.26 g, 40%) as pale yellow solid.

Workup

  1. temperatureslowly warmed the ambient temperature to RT over 30 min

Sources & evidence

ORD record
ord-731ca4aefc0d4e5db5e3dd245ed2c3de
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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