Ethylamine → HCID 178464734, compound

HRID 2064607Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][C:17]([C:19](O)=[O:20])=[CH:18][C:12]=3[N:11]=2)=[N:2]1.[CH:22]([N:25](C(C)C)CC)(C)[CH3:23].C(N)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH2:22]([NH:25][C:19]([C:17]1[CH:16]=[CH:15][C:13]2[NH:14][C:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][N:2]=3)=[N:11][C:12]=2[CH:18]=1)=[O:20])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred solution of [2-(indazol-3-yl)-1H-benzoimidazol-5-yl]-carboxylic acid [130 mg, Example 247(a)], hydroxybenzatriazole (189 mg) and diisopropyl ethylamine (732 μL) in dimethylformamide (3 mL) was treated with ethylamine and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (267 mg). The reaction mixture was heated at 80° C. overnight and then partitioned between ethyl acetate and 5% citric acid. The aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution, then with brine, then dried over magnesium sulfate and then evaporated. The residual oil was subjected to preparative HPLC to give [2-(indazol-3-yl)-1H-benzoimidazol-5-yl]-carboxylic acid, ethylamide as a white solid. LC-MS (METHOD B): RT=2.37 minutes; 306.27 (M+H)+.

Workup

custompartitioned between ethyl acetate and 5% citric acid
extractionThe aqueous layer was re-extracted with ethyl acetate
washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution
dry with materialwith brine, then dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-c745e9f4d15444f192242e91e0ebe624
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288425B2

Reaction notes

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