1,1'-Carbonyldiimidazole → HCID 9910907, compound

HRID 1935337Notes

Reaction equation

[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:27][C@H:28]1[CH2:33][C:32]2[C:34]([N:39]3[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]3)=[CH:35][CH:36]=[C:37]([CH3:38])[C:31]=2[O:30][CH2:29]1>CN(C)C=O>[NH3:2].[CH3:38][C:37]1[C:31]2[O:30][CH2:29][C@@H:28]([NH:27][C:9](=[O:11])[C:8]3[CH:7]=[CH:6][C:5]([C:3]([N:2]([CH3:1])[CH3:14])=[O:4])=[CH:13][CH:12]=3)[CH2:33][C:32]=2[C:34]([N:39]2[CH2:40][CH2:41][N:42]([CH3:45])[CH2:43][CH2:44]2)=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 75 °C

Procedure

4—(Dimethylaminocarbonyl)benzoic acid (described in: Jurewicz, A. T; U.S. Pat. No. 3,607,918, 1971) (38 mg, 0.20 mmol) and 1,1′-carbonyldiimidazole (34 mg , 0.21 mmol) were dissolved in dry N,N-dimethylformamide (4 mL) and stirred at 75° C. for 1.5 h. The reaction mixture was cooled to room temperature and a solution of (S)-3-amino-8-methyl-5-(4-methylpiperazin-1-yl)-3,4-dihydro-2H-1-benzopyran (49 mg, 0.19 mmol) in dry N,N-dimethylformamide (5 mL) was added. The reaction mixture was stirred at 50° C. for 14 h and the solvent was evaporated in vacuo giving 120 mg of a crude product. Purification by preparative TLC using chloroform/methanol/conc. NH3 (95:5:0.5) as the eluent afforded 40 mg (48% yield) of the title compound as a white foam: EIMS (70eV) m/z (relative intensity) 436 (26, M+); [α]21D−9° (c 0.20, chloroform).

Workup

temperatureThe reaction mixture was cooled to room temperature
stirringThe reaction mixture was stirred at 50° C. for 14 h
customthe solvent was evaporated in vacuo
customgiving 120 mg of a crude product
customPurification by preparative TLC

Sources & evidence

ORD record: ord-0e6b4e1afe494c77bd5236d2bbb3e48b
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06387899B1

Reaction notes

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