Ammonia → 4-Amino-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

HRID 2081073ノート

反応式

HRID 2081073 の反応式
[NH3:1].[CH2:2]([O:4][C:5]([C:7]1[C:8]2[S:16][CH:15]=[C:14]([CH2:17][O:18][C:19]3[CH:24]=[C:23]([C:25]4[O:26][C:27]([CH3:30])=[N:28][N:29]=4)[CH:22]=[CH:21][C:20]=3[CH3:31])[C:9]=2[C:10](Cl)=[N:11][CH:12]=1)=[O:6])[CH3:3]>CC(O)C>[CH2:2]([O:4][C:5]([C:7]1[C:8]2[S:16][CH:15]=[C:14]([CH2:17][O:18][C:19]3[CH:24]=[C:23]([C:25]4[O:26][C:27]([CH3:30])=[N:28][N:29]=4)[CH:22]=[CH:21][C:20]=3[CH3:31])[C:9]=2[C:10]([NH2:1])=[N:11][CH:12]=1)=[O:6])[CH3:3]

参加物

4

反応物 2

HCID 222AmmoniaHCID 248007954-Chloro-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

生成物 1

HCID 248100934-Amino-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
140 °C

実験手順

Ammonia gas was bubbled into a solution of 4-chloro-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxy-methyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.12 g, 0.28 mmol) (from Example 12 supra) in 2-propanol (15 mL) for 20 minutes. The mixture was heated in a microwave reactor at 140° C. for 2 hours. The reaction mixture was concentrated. The residue was purified by flash chromatography eluting with 30% ethyl acetate in dichloromethane to give recovered staring material (25 mg) and 4-amino-3-[2-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white powder. (Yield 0.053 g, 44%). HRMS (ES+) m/z Calcd for C21H20N4O4S+H [(M+H)+]: 425.1278. Found: 425.1274.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was purified by flash chromatography
  3. washeluting with 30% ethyl acetate in dichloromethane
  4. customto give
  5. customrecovered

出典と根拠

ORDレコード
ord-3e193f6c0e124be6af38fb971c44b90b
出典データセット
uspto-grants-2011_04
特許番号
US07932390B2

反応ノート

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