1,1'-Carbonyldiimidazole → HCID 22082947, compound

HRID 2187481Notes

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.[NH2:28][C@@H:29]1[CH2:38][CH2:37][C:36]2[C:31](=[C:32]([N:41]3[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]3)[CH:33]=[CH:34][C:35]=2[CH2:39][CH3:40])[CH2:30]1>CN(C)C=O>[NH3:4].[CH2:39]([C:35]1[CH:34]=[CH:33][C:32]([N:41]2[CH2:42][CH2:43][N:44]([CH3:47])[CH2:45][CH2:46]2)=[C:31]2[C:36]=1[CH2:37][CH2:38][C@@H:29]([NH:28][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)[CH2:30]2)[CH3:40]

Participants

Conditions

Temperature: 75 °C

Procedure

4-Morpholinobenzoic acid (64 mg, 0.31 mmol) was dissolved in dry N,N-dimethylformamide (1 mL) and 1,1′-carbonyldiimidazole (52 mg, 0.32 mmol) was added. The reaction mixture was stirred at 75° C. for 1 h and cooled to room temperature. A solution of (R)-2-amino-5-ethyl-8-(4-metylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (80 mg, 0.29 mmol) in dry N,N-dimethylformamide (3 mL) was added and the reaction mixture was stirred at room temperature for 14 h. The solvent was evaporated and the residue was dried in vacuo. The crude product was purified by preparative TLC on silica using chloroform/methanol/conc. NH3 (95:5:0.5) as the eluent which gave 85 mg (59% yield) of the title compound as a white solid: mp 234° C. (dec); EIMS (70 eV) m/z (relative intensity) 462 (27, M+); [α]21D−48° (c 0.09, chloroform).

Workup

temperaturecooled to room temperature
stirringthe reaction mixture was stirred at room temperature for 14 h
customThe solvent was evaporated
customthe residue was dried in vacuo
customThe crude product was purified by preparative TLC on silica

Sources & evidence

ORD record: ord-6b0db06e71094803b744a1cb869c7a1b
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410532B1

Reaction notes

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