Carbon Dioxide → HCID 54551314, compound

HRID 1954809Notes

Reaction equation

[N:1]1([C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2C(O)=O)[CH:5]=[CH:4][CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27](=[O:29])=O.[NH2:30][C@@H:31]1[CH2:40][CH2:39][C:38]2[C:33](=[C:34]([N:41]3[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]3)[CH:35]=[CH:36][CH:37]=2)[CH2:32]1>CN(C)C=O>[CH3:47][N:44]1[CH2:45][CH2:46][N:41]([C:34]2[CH:35]=[CH:36][CH:37]=[C:38]3[C:33]=2[CH2:32][C@H:31]([NH:30][C:27](=[O:29])[C:12]2[CH:11]=[CH:7][C:6]([N:1]4[CH:2]=[CH:3][CH:4]=[CH:5]4)=[CH:14][CH:13]=2)[CH2:40][CH2:39]3)[CH2:42][CH2:43]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 4-(1H-pyrrol-1-ylbenzoic acid (96 mg, 0.51 mmol) in anhydrous N,N-dimethylformamide (25 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-8-(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 ambient temperature for 17 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 128 mg (62% yield) of the title compound as white crystals: mp 245-247° C.; [α]21D -69° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 414 (15, M+).

Workup

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

Sources & evidence

ORD record: ord-b0710b0b27714dbca4e85dfabb6cc92f
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124283

Reaction notes

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