Citric Acid → HCID 67211230, compound

HRID 452146Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:26]=[CH:25][C:11]3/[C:12](=[CH:21]/[C:22](O)=[O:23])/[C:13]4[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=4[CH2:15][CH2:16][C:10]=3[CH:9]=2)[C:5]2[CH:27]=[C:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:29]=[C:30]([CH3:31])[C:4]=2[N:3]=1.[CH3:38][S:39]([NH2:42])(=[O:41])=[O:40].C1CCN2C(=NCCC2)CC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:26]=[CH:25][C:11]3/[C:12](=[CH:21]/[C:22]([NH:42][S:39]([CH3:38])(=[O:41])=[O:40])=[O:23])/[C:13]4[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=4[CH2:15][CH2:16][C:10]=3[CH:9]=2)[C:5]2[CH:27]=[C:28]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:29]=[C:30]([CH3:31])[C:4]=2[N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(E)-[2-(2,4-Dimethyl-6-phenylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetic acid (50 mg, 0.10 mmol) obtained in Example 55 was dissolved in DMF (2 mL), and the mixture was cooled to 0° C. N,N′-carbonyldiimidazole (36 mg, 0.22 mmol) was added, and the mixture was stirred at room temperature for 2 hr. To this mixture were added methanesulfonamide (21 mg, 0.22 mmol) and DBU (21 mg, 0.22 mmol), and the mixture was stirred at 60° C. for 5 hr. 5% Aqueous citric acid solution was added to the mixture, and the precipitate was collected by filtration, and washed with water to give the title compound (compound 57) (31 mg, 55%).

Workup

stirringthe mixture was stirred at 60° C. for 5 hr
filtrationthe precipitate was collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-279e2ffe472e4b89be2b35b9bf191aaf
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486980B2

Reaction notes

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