Acetyl chloride → HCID 66582340, compound

HRID 1972587Notes

Reaction equation

HRID 1972587 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:14][C@@H:13]2[CH2:26][NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:8][CH:7]=1)([OH:5])[CH3:4].CCN(C(C)C)C(C)C.[C:45](Cl)(=[O:47])[CH3:46]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:28]1([N:27]([CH2:26][C@H:13]2[CH2:14][N:15]([S:18]([C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)(=[O:20])=[O:19])[CH2:16][CH2:17][N:12]2[C:9]2[CH:8]=[CH:7][C:6]([C:3]([OH:5])([CH3:4])[C:2]([F:1])([F:34])[F:35])=[CH:11][CH:10]=2)[C:45](=[O:47])[CH3:46])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 665825861,1,1-trifluoro-2-(4-((2S)-2-((phenylamino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

Product 1

HCID 66582340HCID 66582340, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1,1-trifluoro-2-(4-((2S)-2-((phenylamino)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (0.130 g, 0.247 mmol, Example 203) in CH2Cl2 (3.0 mL) was added 4-dimethylaminopyridine (6.1 mg, 0.049 mmol), Hünig's base (0.129 mL, 0.742 mmol), and acetyl chloride (0.035 mL, 0.49 mmol, Aldrich, St. Louis, Mo.). The resulting mixture was stirred at room temperature for 30 min and then the solvent was removed in vacuo. The residue was purified by column chromatography (24 g of silica gel, 10% to 40% EtOAc in hexanes) to afford N-phenyl-N-(((2S)-4-(2-thiophenylsulfonyl)-1-(4-(2,2,2-trifluoro-1-hydroxy-1-methylethyl)phenyl)-2-piperazinyl)methyl)acetamide (0.032 g) as a mixture of two isomers:

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was purified by column chromatography (24 g of silica gel, 10% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-168638a26b2946dbb81c5a117eac08ab
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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