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Hydrochloric Acid → 2-(1-Piperidinylmethyl)-N-[6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

HRID 520657
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HRID 520657 반응식
Cl[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]4[N:26](S(C5C=CC=CC=5)(=O)=O)[CH:27]=[CH:28][C:21]=34)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][N:15]3S(C2C=CC=CC=2)(=O)=O)=[O:9])[N:7]=1.[NH:47]1[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1.[OH-].[Na+].Cl>CC(O)C>[N:47]1([CH2:2][C:3]2[S:4][CH:5]=[C:6]([C:8]([NH:10][C:11]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][N:23]=[C:22]5[NH:26][CH:27]=[CH:28][C:21]=45)[CH:17]=[C:16]4[C:12]=3[CH:13]=[N:14][NH:15]4)=[O:9])[N:7]=2)[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 583563842-(Chloromethyl)-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide

생성물 1

HCID 532334332-(1-Piperidinylmethyl)-N-[6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

시약·촉매·용매

1
HCID 3776Isopropanol용매

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온도
90 °C

실험 절차

2-(Chloromethyl)-N-{1-(phenylsulfonyl)-6-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-indazol-4-yl}-1,3-thiazole-4-carboxamide (40 mg) and piperidine (0.5 ml) were added to a microwave vial then heated in the microwave for 15 min at 90° C. The solvent was blown off under nitrogen. IPA (3 ml) and 2M NaOH (aq) (2 ml) were added and the reaction mixture was stirred for 29 h. The reaction was heated to 50° C. for 5 min then cooled to RT for stirring overnight. The mixture was neutralised to pH 7 with 2M HCl (aq.) and the solvent was removed under a stream of nitrogen. The resultant solid was dissolved in DMSO (2 ml), filtered and purified by MDAP (method K). The fractions were combined and solvent was removed under nitrogen. The residue was dissolved in water:1,4-dioxane (1:1) then freeze-dried to give title compound, as an orange solid, 15 mg.

후처리

  1. temperatureThe reaction was heated to 50° C. for 5 min
  2. temperaturethen cooled to RT
  3. stirringfor stirring overnight
  4. customthe solvent was removed under a stream of nitrogen
  5. dissolutionThe resultant solid was dissolved in DMSO (2 ml)
  6. filtrationfiltered
  7. custompurified by MDAP (method K)
  8. customsolvent was removed under nitrogen
  9. dissolutionThe residue was dissolved in water:1,4-dioxane (1:1)
  10. customthen freeze-dried

출처 및 근거

ORD 기록
ord-3a05c72351404f9aadc21bb222912217
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09326987B2

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