Cesium carbonate → 3-(4-{2-[3-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1505708노트

반응식

HRID 1505708 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13]OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:25][N:26]1[CH:30]=[C:29]([C:31]2[CH:32]=[C:33]([C:37]3[N:42]=[CH:41][C:40]([C:43]4[CH:44]=[N:45][NH:46][CH:47]=4)=[CH:39][N:38]=3)[CH:34]=[CH:35][CH:36]=2)[CH:28]=[N:27]1>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][N:45]2[CH:44]=[C:43]([C:40]3[CH:39]=[N:38][C:37]([C:33]4[CH:34]=[CH:35][CH:36]=[C:31]([C:29]5[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=5)[CH:32]=4)=[N:42][CH:41]=3)[CH:47]=[N:46]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 4183641tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylateHCID 729446552-[3-(1-methyl-1H-pyrazol-4-yl)phenyl]-5-(1H-pyrazol-4-yl)pyrimidine

생성물 1

HCID 899243953-(4-{2-[3-(1-Methyl-1H-pyrazol-4-yl)-phenyl]-pyrimidin-5-yl}-pyrazol-1-ylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester수율 57.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 3-Methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared as described in WO2010100144; 200 mg; 0.64 mmol; 1.0 eq.), cesium carbonate (420 mg; 1.29 mmol; 2.0 eq.) and 2-[3-(1-methyl-1H-pyrazol-4-yl)phenyl]-5-(1H-pyrazol-4-yl)pyrimidine (example 3, 195 mg; 0.64 mmol; 1.0 eq.) was heated at 100° C. O/N. The reaction mixture was then diluted with water and extracted with EtOAc (three times). Combined organic phases were washed with brine (three times), dried over magnesium sulfate, filtered and concentrated. Purification by autopreparative LC/MS afforded the title compound as a white foam (179 mg, 57%). MS (ESI+): 486.5.

후처리

  1. extractionextracted with EtOAc (three times)
  2. washCombined organic phases were washed with brine (three times)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by autopreparative LC/MS

출처 및 근거

ORD 기록
ord-368929df144c4b02a7090b4bcb31e4d8
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216991B2

반응 노트

불러오는 중…