Trifluoroacetic acid → 2-(6-Dimethylaminomethyl-imidazo[1,2-a]pyridin-3-yl)-acetamide

HRID 402889

반응식

HRID 402889 반응식
O.[OH-].[Li+].C([O:6][C:7](=O)[CH2:8][C:9]1[N:13]2[CH:14]=[C:15]([CH2:18][N:19]([CH3:21])[CH3:20])[CH:16]=[CH:17][C:12]2=[N:11][CH:10]=1)C.FC(F)(F)C(O)=O.C(N1C=CN=C1)([N:32]1C=CN=C1)=O>O1CCOCC1.O>[CH3:20][N:19]([CH2:18][C:15]1[CH:16]=[CH:17][C:12]2[N:13]([C:9]([CH2:8][C:7]([NH2:32])=[O:6])=[CH:10][N:11]=2)[CH:14]=1)[CH3:21]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 168937Lithium hydroxide, monohydrateHCID 59192025HCID 59192025, 화합물

생성물 1

HCID 591920412-(6-Dimethylaminomethyl-imidazo[1,2-a]pyridin-3-yl)-acetamide수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

Lithium hydroxide monohydrate (55 mg, 1.31 mmol, 1.5 equiv) is added to a solution of (6-dimethylaminomethyl-imidazo[1,2-a]pyridin-3-yl)-acetic acid ethyl ester (240 mg, 0.87 mmol) in dioxane (10 ml) and water (10 ml). After 1 hour at room temperature, the reaction mixture is concentrated in vacuo. The residue is taken up in N,N-dimethylformamide (10 ml) and treated with trifluoroacetic acid (0.34 ml, 4.5 mmol, 4.5 equiv). Carbonyldiimidazole (167 mg, 0.98 mmol, 1.0 equiv) is added, and the mixture is stirred at room temperature for 1 hour. After removal of the solvent, concentrated aqueous ammonia (10 ml) is added to the activated acid. The mixture is stirred at room temperature for 30 minutes. Volatiles are removed in vacuo, and purification of the residue via flash chromatography (CH2Cl2/MeOH 7:3) affords the title compound (186 mg, 76%). 1H NMR (400 MHz, d4-MeOH): δ=8.31 (s, 1H), 7.55 (d, J=9.0 Hz, 1H), 7.49 (s, 1H), 7.35 (dd, J=9.0/1.5 Hz, 1H), 3.95 (s, 2H), 3.71 (s, 2H), 2.42 (s, 6H). MS (ES+): 233 (M+H)+.

후처리

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. customAfter removal of the solvent, concentrated aqueous ammonia (10 ml)
  3. additionis added to the activated acid
  4. stirringThe mixture is stirred at room temperature for 30 minutes
  5. customVolatiles are removed in vacuo, and purification of the residue via flash chromatography (CH2Cl2/MeOH 7:3)

출처 및 근거

ORD 기록
ord-08bb8308c0f7495cb229da771d7cc79c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742132B2

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