1,1'-Carbonyldiimidazole → HCID 22981584, compound

HRID 427348Notes

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:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)[CH:33]=[CH:34][C:35]=2[CH2:39][O:40][CH3:41])[CH2:30]1>CN(C)C=O>[NH3:4].[CH3:41][O:40][CH2:39][C:35]1[CH:34]=[CH:33][C:32]([N:42]2[CH2:43][CH2:44][N:45]([CH3:48])[CH2:46][CH2:47]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

Participants

Conditions

Temperature: 75 °C

Procedure

4-Morpholinobenzoic acid (54 mg, 0.26 mmol) was dissolved in dry N,N-dimethyl-formamide (1 mL) and 1,1′-carbonyldiimidazole was added. The reaction mixture was stirred at 75° C. for 1.5 h and cooled to room temperature. A solution of (R)-2-amino-5-methoxymethyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (72 mg, 0.25 mmol) in dry N,N-dimethylformamide (3 mL) was added. The reaction mixture was stirred at room temperature for 15 h. The solvent was evaporated giving 160 mg of a crude product. Purification by preparative TLC using chloroformlmethanol/conc. NH3 (95:5:0.5) as the eluent afforded 95 mg (80% yield) of the title compound as a white solid: mp 200° C. (dec); EIMS (70 eV) m/z (relative intensity) 478 (7, M+); [α]21D−46° (c 0.12, chloroform).

Workup

temperaturecooled to room temperature
stirringThe reaction mixture was stirred at room temperature for 15 h
customThe solvent was evaporated
customgiving 160 mg of a crude product
customPurification by preparative TLC

Sources & evidence

ORD record: ord-7a6b168dd5e94afe9f007247e1319fcb
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313118B1

Reaction notes

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