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 2056702ノート

反応式

HRID 2056702 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3763acc293fe42e1b629e1033c9013ca
出典データセット
uspto-grants-2008_02
特許番号
US07335672B2

反応ノート

読み込み中…