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

HRID 402889

反応式

HRID 402889 の反応式
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]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 168937Lithium hydroxide, monohydrateHCID 59192025HCID 59192025、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-08bb8308c0f7495cb229da771d7cc79c
出典データセット
uspto-grants-2014_06
特許番号
US08742132B2

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