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

반응식

HRID 526891 반응식
[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

참가 물질

4

반응물 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

생성물 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-carboxylate수율 55%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
60 °C

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3dc9bcaf090543bc9c50cf17c5763dac
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

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