1,1'-Carbonyldiimidazole → HCID 22082947, compound

HRID 427345Notes

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-dimethylformarnide (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-86e5e30363154f28b3c6c2669071bd45
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313118B1

Reaction notes

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