Carbon Dioxide → HCID 54461367, compound

HRID 2187460Notes

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

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 4-morpholinobenzoic acid (110 mg, 0.51 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 1,1′-carbonyldiimidazole (87 mg, 0.54 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-5-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.49 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added. The reaction was allowed to stir at 70° C. for 18 h and the solvent was evaporated in vacuo. The residue was purified on a silica gel column using chloroform/ethanol saturated with NH3 (100:3) as the eluent. This gave after crystallization from acetonitrile, 65 mg (30% yield) of the title compound as white crystals: mp 127-128° C.; [α]21D +51° (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 434 (14, M+).

Workup

custom(after 30 min)
temperaturethe reaction was cooled to room temperature
customthe solvent was evaporated in vacuo
customThe residue was purified on a silica gel column
customThis gave

Sources & evidence

ORD record: ord-159db988e6cc4162b678edb4ad949252
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410530B1

Reaction notes

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