Acryloyl chloride → HCID 86674084, compound

HRID 337206Notes

Reaction equation

HRID 337206 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:25]=[CH:24][C:23]([C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1.[C:34](Cl)(=[O:37])[CH:35]=[CH2:36]>C1COCC1.C(Cl)Cl>[N:28]1([C:26]([C:23]2[CH:22]=[CH:21][C:20]([S:17]([N:14]3[CH2:15][CH2:16][CH:11]([NH:10][C:34](=[O:37])[CH:35]=[CH2:36])[CH2:12][CH2:13]3)(=[O:19])=[O:18])=[CH:25][CH:24]=2)=[O:27])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 71060126HCID 71060126, compound

Product 1

HCID 86674084HCID 86674084, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (0.33 ml, 1.9 mmol) was added in one portion to a stirred solution of [4-(4-amino-piperidine-1-sulfonyl)-phenyl]-piperidin-1-yl-methanone (0.13 g, 0.39 mmol) in THF (7 ml) followed by the drop wise addition of acryloyl chloride (0.03 ml, 0.43 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 (100 ml) and washed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 100% EtOAc) to give the title compound (0.09 g, 58% yield) as a white powder.

Workup

  1. washwashed sequentially with HCl (1M solution, 50 ml), NaOH (1M solution, 50 ml) and brine (50 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: 100% EtOAc)

Sources & evidence

ORD record
ord-5840d2dd3c1740578598ab57486f8f97
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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