Acryloyl chloride → 4-(4-Acryloylamino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamide

HRID 337220Notes

Reaction equation

HRID 337220 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][CH:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:36]=[CH:35][C:23]([C:24]([NH:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:25])=[C:22]([F:37])[CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1.[C:38](Cl)(=[O:41])[CH:39]=[CH2:40]>C1COCC1.C(Cl)Cl>[C:38]([NH:10][CH:11]1[CH2:12][CH2:13][N:14]([S:17]([C:20]2[CH:36]=[CH:35][C:23]([C:24]([NH:26][CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:25])=[C:22]([F:37])[CH:21]=2)(=[O:18])=[O:19])[CH2:15][CH2:16]1)(=[O:41])[CH:39]=[CH2:40]

Participants

6

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 710600854-(4-Amino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamide

Product 1

HCID 866740874-(4-Acryloylamino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamideYield 25%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (0.51 ml, 3.0 mmol) was added in one portion to a stirred solution of 4-(4-Amino-piperidine-1-sulfonyl)-2-fluoro-N-phenethyl-benzamide (0.24 g, 0.6 mmol) in THF (10 ml), followed by the drop wise addition of acryloyl chloride (0.05 ml, 0.66 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with DCM (20 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered, concentrated and the resulting residue was purified by flash column chromatography (elution: 98% DCM, 2% Methanol) to give the title compound (0.06 g, 25% yield) as a white solid.

Workup

  1. washwashed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe resulting residue was purified by flash column chromatography (elution: 98% DCM, 2% Methanol)

Sources & evidence

ORD record
ord-0667b9706bd5435299fe90ddddf95502
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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