Ammonium Chloride → HCID 25131772, compound

HRID 2262561Notes

Reaction equation

HRID 2262561 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:18]4[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=4)[CH:17]=3)=[C:11]([C:27]([F:30])([F:29])[F:28])[O:10][N:9]=2)=[CH:4][CH:3]=1.Cl.C([N:34]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[Cl-].[NH4+].C(N(CC)C(C)C)(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[N:14]=[CH:15][N:16]([C:18]4[CH:26]=[CH:25][C:21]([C:22]([NH2:34])=[O:23])=[CH:20][CH:19]=4)[CH:17]=3)=[C:11]([C:27]([F:28])([F:29])[F:30])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 25517Ammonium Chloride2×HCID 757711-Hydroxybenzotriazole2×HCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 25131432HCID 25131432, compound

Product 1

HCID 25131772HCID 25131772, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{4-[3-(4-Fluoro-phenyl)-5-trifluoromethyl-isoxazol-4-yl]-imidazol-1-yl}-benzoic acid (90 mg, 0.22 mmol) in THF (4 mL), was added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide HCl (50.7 mg, 0.26 mmol) and N-hydroxybenzotriazole (40.5 mg, 0.0.6 mmol), followed by adding ammonium chloride (40.6 mg, 0.76 mmol) and N,N-diisopropylethylamine (199.2 μL, 1.1 mmol) and the reaction mixture was stirred at room temperature overnight. Then 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide HCl (50.7 mg, 0.26 mmol) and N-hydroxybenzotriazole (40.5 mg, 0.0.6 mmol), followed by adding ammonium chloride (40.6 mg, 0.76 mmol) and N,N-diisopropylethylamine (199.2 μL, 1.1 mmol) was added and the reaction mixture was stirred at room temperature overnight. The mixture was then extracted with ethyl acetate and the combined organic extracts were then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:3 to 0:100) afforded the title compound (38 mg, 42%) which was obtained as a white solid. MS: m/e=417.4 [M+H]+.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. extractionThe mixture was then extracted with ethyl acetate
  4. dry with materialthe combined organic extracts were then dried over sodium sulphate
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=1:3 to 0:100)

Sources & evidence

ORD record
ord-8dee8064aed84c33b948ae1e5c4be25d
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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