Carbon Dioxide → (R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-(N,N-dipropylaminosulphonyl)benzamide

HRID 2187443Notes

Reaction equation

HRID 2187443 reaction equation
[CH2:1]([N:4]([CH2:17][CH2:18][CH3:19])[S:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH2:2][CH3:3].C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[NH2:35][C@@H:36]1[CH2:45][CH2:44][C:43]2[C:38](=[C:39]([N:46]3[CH2:51][CH2:50][N:49]([CH3:52])[CH2:48][CH2:47]3)[CH:40]=[CH:41][CH:42]=2)[CH2:37]1>CN(C)C=O>[CH3:52][N:49]1[CH2:50][CH2:51][N:46]([C:39]2[CH:40]=[CH:41][CH:42]=[C:43]3[C:38]=2[CH2:37][C@H:36]([NH:35][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([S:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:17][CH2:18][CH3:19])(=[O:6])=[O:7])=[CH:16][CH:15]=2)[CH2:45][CH2:44]3)[CH2:47][CH2:48]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 4911ProbenecidHCID 682631,1'-CarbonyldiimidazoleHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54261123(R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-(N,N-dipropylaminosulphonyl)benzamideYield 27.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
75 °C

Procedure

To a solution of 4-(N,N-dipropylaminosulphonyl)benzoic acid (120 mg, 0.43 mmol) in anhydrous N,N-dimethylformamide (25 mL) was added 1,1′-carbonyldiimidazole (73 mg, 0.45 mmol) and the reaction was heated at 75° C. When the carbon dioxide evolution had ceased (after 30 min), the reaction was cooled to room temperature and a solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (100 mg, 0.41 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added. The reaction was allowed to stir at ambient temperature for 24 h and the solvent was evaporated in vacuo. Purification on a silica gel column using chloroform/ethanol saturated with NH3 (100:3) as the eluent gave 58 mg (27% yield) of the title compound as a viscous oil: [α]21D −370 (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 512 (11, M+).

Workup

  1. custom(after 30 min)
  2. temperaturethe reaction was cooled to room temperature
  3. customthe solvent was evaporated in vacuo
  4. customPurification on a silica gel column

Sources & evidence

ORD record
ord-78b28ec916e048a18096a2667c4e9998
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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