Water → HCID 58763579、化合物

HRID 858899ノート

反応式

HRID 858899 の反応式
CO[C:3](=[O:25])[CH:4]([C:8]1[N:12]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]2=[N:10][C:9]=1[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[CH2:5][CH:6]=O.[CH3:26][NH2:27].[BH4-].[Na+].O>CO.CO.CCOC(C)=O>[CH3:26][N:27]1[CH2:6][CH2:5][CH:4]([C:8]2[N:12]3[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)[C:3]1=[O:25]

参加物

7

反応物 4

HCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 58763581HCID 58763581、化合物

生成物 1

HCID 58763579HCID 58763579、化合物収率 19%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 21584119Ethylacetate methanol溶媒

実験手順

To a magnetically stirred solution of 2-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-4-oxo-butyric acid methyl ester 36b (0.035 g, 0.0988 mmol) in methanol (1 mL) at room temperature under Ar atmosphere was added a 40% aqueous solution of methyl amine (0.009 mL, 0.0988 mmol). The reaction mixture was stirred for 1 h at room temperature. NaBH4 (0.0074 g, 0.197 mmol) was added at room temperature. After 30 min, water (30 mL) was added, and the aqueous phase was extracted with EtOAc (2×50 mL). The combined organic layers were dried (MgSO4), and concentrated in vacuo to the crude product. The pure product was obtained by column chromatography over silica gel (EtOAc, then 4:96 MeOH/EtOAc as eluent), which gave the title compound (0.006 g, 19%) as a white solid. (400 MHz, CDCl3) 2.31 (s, 3H), 2.33 (m, 2H), 2.39 (s, 3H), 3.00 (s, 3H), 3.51 (m, 2H), 4.41 (t, J=10.2 Hz, 1H), 7.02 (dd, J=1.1, 9.1 Hz, 1H), 7.24 (d, J=7.7 Hz, 2H), 7.25 (s, 1H), 7.53 (m, 3H).

後処理

  1. waitAfter 30 min
  2. extractionthe aqueous phase was extracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo to the crude product
  5. customThe pure product was obtained by column chromatography over silica gel (EtOAc

出典と根拠

ORDレコード
ord-f093d18b12fb4a7c89c18eaef057c1d0
出典データセット
uspto-grants-2006_12
特許番号
US07148353B2

反応ノート

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