Ethyl Acetate → HCID 15678855, compound

HRID 1110106Notes

Reaction equation

HRID 1110106 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([N:21]2[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[C:25](=[O:32])[NH:24][C:23]3[CH:33]=[CH:34][CH:35]=[N:36][C:22]2=3)=[O:20])[CH2:14][CH2:13]1.[C:37]1([N:46]=[C:47]=[S:48])[CH:42]=[CH:41][CH:40]=[C:39]([N:43]=[C:44]=[S:45])[CH:38]=1.C(OCC)(=O)C>CN(C=O)C>[N:43]([C:39]1[CH:38]=[C:37]([NH:46][C:47]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([N:21]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[C:25](=[O:32])[NH:24][C:23]4[CH:33]=[CH:34][CH:35]=[N:36][C:22]3=4)=[O:20])[CH2:14][CH2:13]2)=[S:48])[CH:42]=[CH:41][CH:40]=1)=[C:44]=[S:45]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 18404Isothiocyanic acid, m-phenylene esterHCID 15678852HCID 15678852, compound

Product 1

HCID 15678855HCID 15678855, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,11-Dihydro-11-[(4-[10-aminodecyl]-1-piperazinyl)acetyl]-6H-pyrido[2,3-b][1,4]-benzodiazepine-6-one (2.8 mg, 5.7 μmol) was dissolved in 0.2 mL DMF and treated with 1,3-phenylenediisothiocyanate (6 mg, 31 μmol). After 0.5 h, ethyl acetate (1 mL) and petroleum ether (3 mL) were added, and the cloudy mixture was stored at 4° C. overnight. The supernatant was decanted from the oily residue. The residue solidified upon trituration with dry ether to give 2.0 mg (51% yield) of pure product (Rf =0.35, silica, chloroform:methanol:acetic acid, 85:10:5, by volume). FAB-MS spectrum showed a parent ion peak at 685 m/z (m+1).

Workup

  1. waitthe cloudy mixture was stored at 4° C. overnight
  2. customThe supernatant was decanted from the oily residue

Sources & evidence

ORD record
ord-e44c58059c7e41e2aa3f2cb3c92b86b9
Source dataset
uspto-grants-1994_06
Patent number
US05324832

Reaction notes

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