Water → HCID 66965832, compound

HRID 1514895Notes

Reaction equation

HRID 1514895 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[C:10]1[NH:11][C:12]2[CH:18]=[C:17]([C:19](Cl)=[O:20])[CH:16]=[CH:15][C:13]=2[N:14]=1.[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[NH2:32].CCN(C(C)C)C(C)C.O>CCOC(C)=O>[CH:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][C:23]=1[NH:32][C:19]([C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([C:4]3[C:3]([CH3:2])=[CH:8][CH:7]=[CH:6][C:5]=3[CH3:9])[NH:11][C:12]=2[CH:18]=1)=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 70572-NaphthylamineHCID 81531DiisopropylethylamineHCID 87217357HCID 87217357, compound

Product 1

HCID 66965832HCID 66965832, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 2-(2,6-dimethylphenyl)-3H-benzoimidazole-5-carbonyl chloride HCl salt (160 mg) and naphthalen-2-ylamine (72 mg) was added DIPEA (0.27 mL). The resulting solution was stirred for at room temperature for 18 h then the mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated. The residue was purified by an amino column using hexanes/ethyl acetate (1:4) as eluent and gave 2-(2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid naphthalen-2-ylamide as a white solid; MS (ESI)m/z 392 (M+H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by an amino column

Sources & evidence

ORD record
ord-e692a2128dfa419cbb395c95c51f8d86
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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