Carbon Dioxide → HCID 54462702, compound

HRID 1862043Notes

Reaction equation

HRID 1862043 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(=O)=O.[NH2:31][C@@H:32]1[CH2:41][CH2:40][C:39]2[C:34](=[C:35]([N:44]3[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]3)[CH:36]=[CH:37][C:38]=2[O:42][CH3:43])[CH2:33]1>CN(C)C=O>[CH3:43][O:42][C:38]1[CH:37]=[CH:36][C:35]([N:44]2[CH2:45][CH2:46][N:47]([CH3:50])[CH2:48][CH2:49]2)=[C:34]2[C:39]=1[CH2:40][CH2:41][C@@H:32]([NH:31][C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:15][CH:14]=1)[CH2:33]2

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 682631,1'-CarbonyldiimidazoleHCID 3452784-(Morpholin-4-yl)benzoic acidHCID 54422599HCID 54422599, compound

Product 1

HCID 54462702HCID 54462702, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-morpholinobenzoic acid (0.92 g, 4.5 mmol; described in: Degutis, J.;Rasteikiene, L.; Degutiene, A. Zh. Org. Khim. 1978, 14(10), 2060-2064) in anhydrous N,N-dimethylformarnride (75 mL) was added 1,1′-carbonyldiimidazole (0.76 g, 4.8 mrnol) and the reaction was heated at 75° C. When the carbon dioxide evolution had ceased (after 45 min), the reaction was cooled to room temperature and a solution of (R)-2-arnino-5-methoxy-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (1.2 g, 4.2 mmol) dissolved in anhydrous N,N-dimethylformamide (20 mL) was added. The reaction was allowed to stir at ambient temperature for 48 h and the solvent was evaporated in vacuo. Purification on a silica gel column using chloroform/methanol/concentrated ammonium hydroxide (180:5:0.5) as the eluent followed by recrystallization from ethyl acetate and a few drops of methanol gave 1.0 g (53% yield) of white crystals: mp 237-238° C. [α]21D+40° (c=1,1chloroform); EIMS (70 eV) m/z (relative intensity) 464 (5, M+).

Workup

  1. custom(after 45 min)
  2. temperaturethe reaction was cooled to room temperature
  3. additionwas added
  4. customthe solvent was evaporated in vacuo
  5. customPurification on a silica gel column
  6. customfollowed by recrystallization from ethyl acetate and a few drops of methanol

Sources & evidence

ORD record
ord-6ea9ca867c14414eb8c73f358293efe5
Source dataset
uspto-grants-2003_03
Patent number
US06534652B2

Reaction notes

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