Diisopropylethylamine → HCID 9828394, compound

HRID 906635Notes

Reaction equation

HRID 906635 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH2:9][C:10]2[S:11][C:12]([S:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:35]1(/[CH:41]=[CH:42]/[C:43](Cl)=[O:44])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH2:9][C:10]2[S:11][C:12]([S:15]([N:18]3[CH2:23][CH2:22][N:21]([C:43](=[O:44])/[CH:42]=[CH:41]/[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:20][CH2:19]3)(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5354261Cinnamoyl ChlorideHCID 9952792Benzamide, 4-chloro-N-[[5-(1-piperazinylsulfonyl)-2-thienyl]methyl]-

Product 1

HCID 9828394HCID 9828394, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1 (36 mg, 0.09 mmol) and iPr2NEt (32 μl, 0.189 mmol) in CHCl3 (2 mL) was added [(2E)-3-phenylprop-2-enoyl]chloride (15 mg, 0.09 mmol). After 4 h the reaction mixture was washed with HCl (1 N) and sat. NaCl solution, and dried over MgSO4. The solvent was evaporated and the residue was filtered through silica gel using AcOEt/MeOH 1% as eluent to afford 159 as white solid (10 mg, 20%). M/Z APCI: 531.2 (M+1), 529.1 (M−1). Anal. HPLC: rt.=6.18 min (method a).

Workup

  1. washAfter 4 h the reaction mixture was washed with HCl (1 N) and sat. NaCl solution
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated
  4. filtrationthe residue was filtered through silica gel

Sources & evidence

ORD record
ord-637a0d0c1f2e4658a8bfc3c2ea3293e5
Source dataset
uspto-grants-2011_09
Patent number
US08012995B1

Reaction notes

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