1-Ethyl-3-piperidinol → Trifluoroacetic acid

HRID 2056707Notes

Reaction equation

HRID 2056707 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][C:9]2[C:14]3[N:15]=[C:16]([NH:18]C(=O)C)[S:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[N:3]=1.[CH2:32]([N:34]1[CH2:39][CH2:38][CH2:37][CH:36]([OH:40])[CH2:35]1)[CH3:33].[C:41]([O-:44])(O)=[O:42].[Na+]>C(O)C>[CH2:32]([N:34]1[CH2:39][CH2:38][CH2:37][CH:36]([O:40][C:2]2[N:7]=[C:6]([O:8][C:9]3[C:14]4[N:15]=[C:16]([NH2:18])[S:17][C:13]=4[CH:12]=[CH:11][CH:10]=3)[CH:5]=[C:4]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:26][CH:27]=3)[N:3]=2)[CH2:35]1)[CH3:33].[C:41]([OH:44])([C:28]([F:31])([F:30])[F:29])=[O:42]

Participants

6

Reactant 3

HCID 1145241-Ethyl-3-piperidinolHCID 516892Sodium BicarbonateHCID 58612070N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzo[d]thiazol-2-yl}-acetamide

Product 2

HCID 6422Trifluoroacetic acidHCID 115191594-(2-(1-Ethylpiperidin-3-yloxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzo[d]thiazol-2-yl}-acetamide (70 mg, 0.15 mmol, Example 7(d)) and 1-ethyl-3-hydroxypiperidine (39 mg, 0.3 mmol, Aldrich) in ethanol (1 mL) was heated in a microwave synthesizer at 140° C. for 20 min. The reaction mixture was diluted with sat. aqueous solution of NaHCO3 (10 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (20 mL), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo and the residue was purified by preparative HPLC [gradient 20-80% MeCN (0.1% TFA)/H2O (0.1% TFA)] to give the title compound as a salt with TFA. MS (ESI, pos. ion) m/z: 516 (M+1).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic extracts were washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by preparative HPLC [gradient 20-80% MeCN (0.1% TFA)/H2O (0.1% TFA)]

Sources & evidence

ORD record
ord-f33bd537b33f4928b80c824cfe7add84
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

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