Acryloyl chloride → HCID 86674085, compound

HRID 337209Notes

Reaction equation

HRID 337209 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]([CH:22]2[CH2:24][CH2:23]2)=[O:21])[CH2:15][CH2:14]3)(=[O:10])=[O:9])[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.[C:34](Cl)(=[O:37])[CH:35]=[CH2:36]>C1COCC1.CCOC(C)=O>[CH:22]1([C:20]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([S:8]([N:5]4[CH2:6][CH2:7][CH:2]([NH:1][C:34](=[O:37])[CH:35]=[CH2:36])[CH2:3][CH2:4]4)(=[O:10])=[O:9])=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)=[O:21])[CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 71079564HCID 71079564, compound

Product 1

HCID 86674085HCID 86674085, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

[5-(4-Amino-piperidine-1-sulfonyl)-2,3-dihydro-indol-1-yl]-cyclopropyl-methanone (0.09 g, 0.25 mmol) was dissolved in THF (5 ml). To this was added diisopropylethylamine (0.2 ml, 1.0 mmol) in one portion followed by the drop wise addition of acryloyl chloride (0.02 ml, 0.27 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was diluted with EtOAc (50 ml) and washed sequentially with HCl (1M solution, 20 ml), NaOH (1M solution, 20 ml) and brine (20 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 (0.035 g, 35% yield) as a white powder.

Workup

  1. washwashed sequentially with HCl (1M solution, 20 ml), NaOH (1M solution, 20 ml) and brine (20 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-907131362ee0473abd81b5fb2fa0eb92
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

Loading…