Sodium methanolate methanol → (S)-tetrahydrofuran-3-yl 3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate

HRID 526891

反応式

HRID 526891 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:21][N:20]([C:22]([O:24][C@H:25]5[CH2:29][CH2:28][O:27][CH2:26]5)=[O:23])[CH2:19]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.C[O-].[Na+].CO>CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH:17][CH:18]4[CH2:19][N:20]([C:22]([O:24][C@H:25]5[CH2:29][CH2:28][O:27][CH2:26]5)=[O:23])[CH2:21]4)[C:14]([F:30])=[CH:13][N:12]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 23694274Sodium methanolate methanolHCID 67287100(S)-tetrahydrofuran-3-yl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate

生成物 1

HCID 68007196(S)-tetrahydrofuran-3-yl 3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate収率 55%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

(S)-tetrahydrofuran-3-yl 3-(2-(5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)azetidine-1-carboxylate, 6d, was dissolved in methanol (2 mL) and then treated with of 25% sodium methoxide/methanol (0.5 mL) and heated at 60° C. in sealed tube. LCMS showed complete reaction after 10 minutes. The resulting solution was quenched with aqueous saturated NH4Cl solution (0.5 mL) then evaporated to dryness and the residue dissolved in DMSO and purified by reverse phase HPLC (ammonium formate buffer) to afford 25.9 mg (55% yield) of the desired product, 422, as a solid.

後処理

  1. customreaction after 10 minutes
  2. customThe resulting solution was quenched with aqueous saturated NH4Cl solution (0.5 mL)
  3. customthen evaporated to dryness
  4. dissolutionthe residue dissolved in DMSO
  5. custompurified by reverse phase HPLC (ammonium formate buffer)

出典と根拠

ORDレコード
ord-3dc9bcaf090543bc9c50cf17c5763dac
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

関連ノート

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