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Hydrochloric Acid → HCID 59471935、化合物

HRID 2204863
ノート
印刷プレビュー

反応式

HRID 2204863 の反応式
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:17]3[C:22]([NH2:23])=[N:21][CH:20]=[C:19]([C:24]4[CH:29]=[CH:28][C:27]([C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[CH:26][CH:25]=4)[N:18]=3)=[N:15][N:16]=2)=[CH:8][CH:7]=1)(=O)C.[OH-].[Na+].Cl>CO>[NH2:23][C:22]1[N:21]=[CH:20][C:19]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([N:31]([CH3:33])[CH3:32])=[O:34])=[CH:26][CH:25]=2)=[N:18][C:17]=1[C:14]1[O:13][C:12]([C:9]2[CH:8]=[CH:7][C:6]([CH2:5][OH:4])=[CH:11][CH:10]=2)=[N:16][N:15]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59471775[4-[5-[3-Amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl acetate

生成物 1

HCID 59471935HCID 59471935、化合物収率 71.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
55 °C

実験手順

[4-[5-[3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl acetate (118 mg, 0.2445 mmol) was suspended in methanol (2 mL) and treated with NaOH (489.0 μL of 1 M, 0.4890 mmol). The resulting mixture was stirred at 55° C. for 1 h. The reaction mixture was cooled to room temperature and then neutralised with HCl (978.0 μL of 1 M, 0.9780 mmol), filtered and washed with acetonitrile. The resulting yellow powder was heated in acetonitrile (5 mL), cooled and filtered to give a pale yellow powder. This was purified by column chromatography on silica gel eluting with 5% MeOH/CH2Cl2 to give the product as a pale yellow powder (73 mg, 70%); 1H NMR (400 MHz, DMSO) d 2.98-3.02 (m, 6H), 4.64 (d, 2H), 5.44 (t, 1H), 7.54-7.62 (dd, 4H), 7.78 (br s, 2H), 8.12-8.18 (dd, 4H) and 8.98 (s, 1H) ppm; MS (ES+) 417.23

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with acetonitrile
  4. temperatureThe resulting yellow powder was heated in acetonitrile (5 mL)
  5. temperaturecooled
  6. filtrationfiltered
  7. customto give a pale yellow powder
  8. customThis was purified by column chromatography on silica gel eluting with 5% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-9177d2ddc48a44b9adb500a7e39309db
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365557B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート