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 879289Notes

Reaction equation

HRID 879289 reaction equation
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]

Participants

3

Reactant 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

Product 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

Conditions

Temperature
120 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-595ab9beef3f4f0d9dfbfe493d24f0aa
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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