Acryloyl chloride → HCID 52939643, compound

HRID 1841939Notes

Reaction equation

HRID 1841939 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:37](Cl)(=[O:40])[CH:38]=[CH2:39]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:27])[NH:10][CH:11]1[CH2:12][CH2:13][N:14]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:37](=[O:40])[CH:38]=[CH2:39])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:15][CH2:16]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 56953988HCID 56953988, compound

Product 1

HCID 52939643HCID 52939643, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid benzyl ester (1.29 g, 3.3 mmol) was dissolved in DCM (20 ml). To this was added diisopropylethylamine (1.64 ml, 9.9 mmol) in one portion followed by the drop wise addition of acryloyl chloride (0.3 ml, 3.6 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. The THF was removed under vacuum and the resulting crude material was purified by Prep HPLC to give the title compound (10.4 mg, 1% yield) as a white powder.

Workup

  1. customThe THF was removed under vacuum
  2. customthe resulting crude material was purified by Prep HPLC

Sources & evidence

ORD record
ord-b02774a06dc2489ba6a2eb0ef5680843
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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