Aniline → HCID 67211557, compound

HRID 452159Notes

Reaction equation

HRID 452159 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.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:39]1([NH:38][C:22](=[O:23])/[CH:21]=[C:12]2\[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[CH2:15][CH2:16][C:10]3[CH:9]=[C:8]([CH2:7][N:6]4[C:5]5[CH:27]=[C:28]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)[CH:29]=[C:30]([CH3:31])[C:4]=5[N:3]=[C:2]4[CH3:1])[CH:26]=[CH:25][C:11]\2=3)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 67210973HCID 67210973, compound

Product 1

HCID 67211557HCID 67211557, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-[2-(2,4-Dimethyl-6-phenylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetic acid (0.050 g, 0.103 mmol) obtained in Example 55 was dissolved in DMF (1 mL), aniline (0.018 mL, 0.200 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.047 g, 0.240 mmol) and 1-hydroxybenzotriazole (0.032 g, 0.240 mmol) were added, and the mixture was stirred at room temperature for 15 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture, and the precipitated solid was collected by suction filtration to give the title compound (compound 90) (0.048 g, 83%).

Workup

  1. filtrationthe precipitated solid was collected by suction filtration

Sources & evidence

ORD record
ord-283a8410c60a4720846dfdae99bdea11
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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