Ethylamine → HCID 178464734, compound

HRID 2182365Notes

Reaction equation

HRID 2182365 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

6

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524162HCID 178524162, compound

Product 1

HCID 178464734HCID 178464734, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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)+. (b) [2-(Indazol-3-yl)-1H-benzoimidazol-5-yl]-carboxylic acid, methylamide

Workup

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

Sources & evidence

ORD record
ord-66e507412bf3409d973e7f41e702cd22
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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