Potassium Hydroxide → Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

HRID 712311ノート

反応式

HRID 712311 の反応式
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]#[C:17][Si](C)(C)C)=[CH:14][C:13]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[CH2:33][CH2:32][C:31]([CH3:39])([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30][CH2:29]4)=[N:26][CH:27]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[OH-].[K+]>CCO>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]#[CH:17])=[CH:14][C:13]([C:22]3[CH:27]=[N:26][C:25]([N:28]4[CH2:29][CH2:30][C:31]([CH3:39])([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:32][CH2:33]4)=[N:24][CH:23]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 86664024Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(2-trimethylsilylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

生成物 1

HCID 86663977Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate収率 83.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To an ice-cold solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(2-trimethylsilylethynyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (1.1 g, 1.94 mmol) in EtOH (40 mL) was added powdered KOH (0.24 g, 4.21 mmol) and the mixture stirred at rt for 4 h. After completion of reaction (by TLC), the solvent was evaporated under reduced pressure, water added and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine and water then dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure to obtain the product as a pale yellow solid (0.8 g, 83% yield). 1H NMR (DMSO-d6): δ 1.11 (t, J=7.20 Hz, 3H), 1.21 (m, 6H), 1.42 (m, 2H), 2.04 (m, 2H), 3.20 (m, 2H), 3.33 (q, J=7.20, 2H), 4.13 (q, J=6.80 Hz, 2H), 4.25 (m, 2H), 4.67 (s, 1H), 6.80 (br s, 1H), 7.61 (s, 1H), 7.94 (s, 1H); 8.78 (s, 2H) and 10.86 (br s, 1H). MS: 493.12 [M+H]+.

後処理

  1. customAfter completion of reaction (by TLC)
  2. customthe solvent was evaporated under reduced pressure, water
  3. additionadded
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined organic layer was washed with brine and water
  6. dry with materialthen dried over anhydrous Na2SO4
  7. customSolvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-9037c72c665048ea847e609e8cafdcb4
出典データセット
uspto-grants-2015_11
特許番号
US09181234B2

反応ノート

読み込み中…