Cesium carbonate → HCID 70169281、化合物

HRID 1426984ノート

反応式

HRID 1426984 の反応式
Cl[CH2:2][C@@H:3]([OH:31])[CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH:20]([OH:22])[CH2:19][C@@H:18]3[C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[OH:30])=[N:13][C:12]=12)=[O:7].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:29][C:27]1[CH:26]=[CH:25][C:24]2[O:30][CH2:2][C@@H:3]([OH:31])[CH2:4][NH:5][C:6](=[O:7])[C:8]3=[C:12]4[N:13]=[C:14]([CH:15]=[CH:16][N:11]4[N:10]=[CH:9]3)[N:17]3[C@H:18]([CH2:19][C@@H:20]([OH:22])[CH2:21]3)[C:23]=2[CH:28]=1

参加物

4

反応物 2

HCID 10796Cesium carbonateHCID 67471069N-((S)-3-chloro-2-hydroxypropyl)-5-((R)-2-(5-fluoro-2-hydroxyphenyl)-4-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

生成物 1

HCID 70169281HCID 70169281、化合物収率 16.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A mixture of N-((S)-3-chloro-2-hydroxypropyl)-5-((R)-2-(5-fluoro-2-hydroxyphenyl)-4-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (0.0407 g, 0.0778 mmol) and Cs2CO3 (0.127 g, 0.389 mmol) in DMF (3.6 mL) was heated at 85° C. for 30 minutes. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated under reduced pressure to give the crude material which was purified by silica column chromatography, eluting with 0-20% MeOH/EtOAc to afford the crude product. The crude material was purified using chiral column chromatography (Chiral Tech OD-H column, 20% EtOH in hexanes). Isolation of the material having a retention time of about 21.8 minutes afforded the title compound (0.0052 g, 16.2% yield). The stereochemistry of the title compound was confirmed by 1H-NMR nOe experiment. LC/MS (ES+APCI) m/z=414.1 (M+H).

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give the crude material which
  5. customwas purified by silica column chromatography
  6. washeluting with 0-20% MeOH/EtOAc
  7. customto afford the crude product
  8. customThe crude material was purified

出典と根拠

ORDレコード
ord-33e093160c4c439cbd02921a921bfec5
出典データセット
uspto-grants-2015_01
特許番号
US08933084B2

反応ノート

読み込み中…