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 1505708ノート

反応式

HRID 1505708 の反応式
[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]

参加物

5

反応物 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

生成物 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 ester収率 57.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-368929df144c4b02a7090b4bcb31e4d8
出典データセット
uspto-grants-2015_12
特許番号
US09216991B2

反応ノート

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