3,3-Difluoropyrrolidine → HCID 59341855、化合物

HRID 16009

反応式

HRID 16009 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([N:21]5[CH2:25][CH2:24][C:23](=O)[CH2:22]5)=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.FC1(F)CC[NH:30][CH2:29]1>O1CCCC1.CO.CC(N(C)C)=O>[CH3:29][NH:30][C@@H:23]1[CH2:24][CH2:25][N:21]([C:18]2[N:17]=[C:16]3[N:12]([CH2:11][C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:1]=[CH:2][CH:3]=[CH:4]5)[N:13]=[N:14][C:15]3=[N:20][CH:19]=2)[CH2:22]1

参加物

4

反応物 2

HCID 27828273,3-DifluoropyrrolidineHCID 593418151-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-one

生成物 1

HCID 59341855HCID 59341855、化合物収率 46.2%

試薬・触媒・溶媒 1

HCID 86616412Tetrahydrofuran methanol dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

A suspension of 1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-one (50 mg, 0.15 mmol) and 3,3-difluoropyrrolidine (42 mg, 0.29 mmol) in tetrahydrofuran/methanol/dimethylacetamide (1.0 mL each) was heated to 80° C. for 2 hours then NaBCNH3 (18 mg, 0.29 mmol) was added. After 2 hours the solution was cooled to room temperature and concentrated. The crude product was purified by flash chromatography using a Horizon purification system on a 25S column eluting with chloroform/acetone (5-50%) followed by a second column on a 12M cartridge eluting with chloroform/ethyl acetate (25-100%) to afford the title compound (25 mg, 40%).

後処理

  1. additionNaBCNH3 (18 mg, 0.29 mmol) was added
  2. temperatureAfter 2 hours the solution was cooled to room temperature
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography
  5. customa Horizon purification system on a 25S column
  6. washeluting with chloroform/acetone (5-50%)
  7. washeluting with chloroform/ethyl acetate (25-100%)

出典と根拠

ORDレコード
ord-5c3e3bb1ce0c4d1096cbf35ede4881e8
出典データセット
uspto-grants-2010_06
特許番号
US07732604B2

関連ノート

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