Ammonia → HCID 178488852, compound

HRID 1108601Notes

Reaction equation

HRID 1108601 reaction equation
N.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:18]2[NH:22][C:21]3[CH:23]=[CH:24][C:25]([C:27](O)=[O:28])=[CH:26][C:20]=3[N:19]=2)=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9]2.Cl.C[N:32](C)CCCN=C=NCC>O1CCOCC1.CN(C)C1C=CN=CC=1>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:18]2[NH:22][C:21]3[CH:23]=[CH:24][C:25]([C:27]([NH2:32])=[O:28])=[CH:26][C:20]=3[N:19]=2)=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]([F:17])([F:15])[F:16])[CH:10]=[CH:9]2

Participants

6

Reactant 3

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178488853HCID 178488853, compound

Product 1

HCID 178488852HCID 178488852, compoundYield 13.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ammonia (0.5M in 1,4-dioxane, 3.9 ml) was added to a stirred solution of 2-(8-methoxy-2-trifluoromethylquinolin-5-yl)-1H-benzimidazole-5-carboxylic acid (0.15 g) in 1,4-dioxane (30 ml) at room temperature under an inert atmosphere. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g) was added followed by 4-dimethylaminopyridine (36 mg) and the reaction stirred at room temperature overnight. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (2×40 ml) and water (50 ml). The combined organic phases were dried over magnesium sulphate and preadsorbed onto silica in vacuo. Purification by column chromatography eluting with 10% methanol in ethyl acetate afforded the title compound as a cream solid (20 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (2×40 ml) and water (50 ml)
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. customPurification by column chromatography
  5. washeluting with 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-e6ba5c5ff9134714b09d15173a1e481b
Source dataset
uspto-grants-2000_05
Patent number
US06069151

Reaction notes

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