Acetyl chloride → HCID 23144572, compound

HRID 337453Notes

Reaction equation

HRID 337453 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[S:13][C:12]([NH2:14])=[N:11][C:10]=1[C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)=[O:8].[C:20](Cl)(=[O:22])[CH3:21]>N1C=CC=CC=1>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:10]1[N:11]=[C:12]([NH:14][C:20](=[O:22])[CH3:21])[S:13][C:9]=1[C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 23144251HCID 23144251, compound

Product 1

HCID 23144572HCID 23144572, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 186 (300 mg, 1.11 mmol) was dissolved in pyridine (3.7 mL), and acetyl chloride (0.130 mL, 1.89 mmol) and N,N-dimethylaminopyridine (6.75 mg, 0.0553 mmol) were added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=2:1) to afford the entitled Compound 188 (233 mg, 67%) as a pale yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c1e93470d17e463f9e195b2ee9e1e0bc
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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