tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(4-(2-acetamidobenzo[d]thiazol-4-yloxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 2056702Notes

Reaction equation

HRID 2056702 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:19](=[O:21])[CH3:20])[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.[N:32]1([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C(O)C>[C:19]([NH:18][C:16]1[S:17][C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([O:8][C:6]3[CH:5]=[C:4]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)[N:3]=[C:2]([N:35]4[CH2:34][CH2:33][N:32]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:37][CH2:36]4)[N:7]=3)[C:14]=2[N:15]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 58612070N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzo[d]thiazol-2-yl}-acetamide

Product 1

HCID 11520080Tert-butyl 4-(4-(2-acetamidobenzo[d]thiazol-4-yloxy)-6-(4-(trifluoromethyl)phenyl)pyrimidin-2-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of N-{4-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide (186 mg, 0.4 mmol, Example 7(d)) and tert-butyl 1-piperazine-carboxylate (149 mg, 0.8 mmol, Aldrich) in ethanol (1 mL) was heated in a microwave synthesizer at 125° C. for 40 min. The reaction mixture was evaporated under reduced pressure and the residue was treated with sat. aqueous solution of NaHCO3 (10 mL), and extracted with EtOAc (2×30 mL). The combined EtOAc extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (20% EtOAc/hexane) to give the title compound as a solid. MS (ESI, pos. ion) m/z: 615 (M+1). M.p.: 211° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionthe residue was treated with sat. aqueous solution of NaHCO3 (10 mL)
  3. extractionextracted with EtOAc (2×30 mL)
  4. washThe combined EtOAc extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-3763acc293fe42e1b629e1033c9013ca
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

Loading…