1-Methylpiperazine → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)phenyl)benzo[d]thiazol-6-yl)ethanol

HRID 879289ノート

反応式

HRID 879289 の反応式
C([O:7][CH2:8][C@@H:9]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[C:10]1[C:31]([CH3:32])=[CH:30][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[CH:28]=[CH:27][N:26]=[C:25](Cl)[CH:24]=4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)(=O)C(C)(C)C.[CH3:45][N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>>[C:41]([O:40][C@@H:9]([C:10]1[C:31]([CH3:32])=[CH:30][C:13]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([N:49]5[CH2:50][CH2:51][N:46]([CH3:45])[CH2:47][CH2:48]5)[CH:24]=4)[CH:18]=3)[S:16][C:12]=2[C:11]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[CH2:8][OH:7])([CH3:43])([CH3:44])[CH3:42]

参加物

3

反応物 2

HCID 531671-MethylpiperazineHCID 86699806(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(2-chloropyridin-4-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate

生成物 1

HCID 86699807(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(3-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)phenyl)benzo[d]thiazol-6-yl)ethanol

反応条件

温度
120 °C

実験手順

The reaction mixture of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(3-(2-chloropyridin-4-yl)phenyl)-5-methylbenzo[d]thiazol-6-yl)ethyl pivalate (16 mg, 0.025 mmol), 1-methylpiperazine (1 mL) was heated at 120° C. overnight. Then the reaction mixture was washed by sat. NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated. To the residue was added THF, MeOH, 2N NaOH, the mixture was heated at 45° C. After the reaction finished, the reaction was washed by sat NaHCO3, extracted by EtOAc, the organic phase was dried over MgSO4, filtered, concentrated down and purified by silica gel column, eluting by 0-100% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C36H39ClN4O2S: 627.2 (M+H+); Found: 627.3 (M+H+).

後処理

  1. washThen the reaction mixture was washed by sat. NaHCO3
  2. extractionextracted by EtOAc
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionTo the residue was added THF, MeOH, 2N NaOH
  7. temperaturethe mixture was heated at 45° C
  8. washthe reaction was washed
  9. extractionextracted by EtOAc
  10. dry with materialthe organic phase was dried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated down
  13. custompurified by silica gel column
  14. washeluting by 0-100% EtOAc in hexanes
  15. customto give the product

出典と根拠

ORDレコード
ord-595ab9beef3f4f0d9dfbfe493d24f0aa
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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