Methanol → (S)-2-(3,5-dichlorophenylamino)-1-(3-(ethyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone

HRID 919584ノート

反応式

HRID 919584 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([N:19]([CH2:39][CH3:40])[C:20]3[C:21]4[CH:28]=[CH:27][N:26](S(C5C=CC(C)=CC=5)(=O)=O)[C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].CO>CO.O.C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([N:19]([CH2:39][CH3:40])[C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:14]2)=[O:12])[CH:3]=[C:2]([Cl:1])[CH:7]=1

参加物

6

反応物 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86706457(S)-2-(3,5-dichlorophenylamino)-1-(3-(ethyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone

生成物 1

HCID 56971627(S)-2-(3,5-dichlorophenylamino)-1-(3-(ethyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone収率 50.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
60 °C

実験手順

To a solution of (S)-2-(3,5-dichlorophenylamino)-1-(3-(ethyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl) ethanone (70 mg, 0.11 mmol) in MeOH:H2O (4:1, 10 mL), K2CO3 (48 mg, 0.35 mmol) was added and the reaction mixture was heated at 60° C. for 1 h, the reaction was monitored by TLC. After completion of reaction, the reaction mixture was concentrated under vacuo to give a residue. The residue triturated with 10% MeOH in EtOAc (15 mL), the suspension was filtrated, the filtrate was evaporated under vacuo to give the crude compound that was subjected to column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford (25 mg, 45%) of the titled compound. 1H NMR (400 MHz, DMSO-d6): δ 11.79 and 11.6 (2s, 1H), 8.106 (d, J=6.8 Hz, 1H), 7.18 and 7.13 (2s, 1H), 6.76 (s, 1H), 6.69 (s, 1H), 6.62 (s, 1H), 6.49 and 6.43 (2s, 1H), 6.37 and 6.33 (2t, J=2.3 Hz, 1H), 4.74-4.69 (m, 1H), 4.46-4.39 (m, 1H), 4.13-3.88 (m, 4H), 3.76-3.70 (m, 2H), 3.20-3.16 (m, 1H), 3.00 (t, J=12.0 Hz, 1H), 2.86 (t, J=12.0 Hz, 1H), 2.62 (t, J=13.6 Hz, 1H), 1.98-1.81 (m, 3H), 1.65-1.49 (m, 1H), 1.19 (t, J=6.8 Hz, 3H). LC-MS: m/z [M+1]=447. HPLC (254 nm): 97.68%. HPLC (210 nm): 98.20%.

後処理

  1. customAfter completion of reaction
  2. concentrationthe reaction mixture was concentrated under vacuo
  3. customto give a residue
  4. customThe residue triturated with 10% MeOH in EtOAc (15 mL)
  5. filtrationthe suspension was filtrated
  6. customthe filtrate was evaporated under vacuo
  7. customto give the crude compound that

出典と根拠

ORDレコード
ord-a6a7ebae2ccb4252804306d775792757
出典データセット
uspto-grants-2016_03
特許番号
US09273028B2

反応ノート

読み込み中…