Hydrochloric Acid → HCID 178486084, 화합물

HRID 1485647노트

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HRID 1485647 반응식
[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@@H:9]([O:10][C:11]3[N:39](COCC[Si](C)(C)C)[C:14]4=[N:15][C:16]([C:20]5[CH:25]=[CH:24][C:23]([C:26]6[CH:31]=[CH:30][C:29]([N:32]=[S:33]([CH3:38])([N:35]([CH3:37])[CH3:36])=[O:34])=[CH:28][CH:27]=6)=[CH:22][CH:21]=5)=[C:17]([Cl:19])[CH:18]=[C:13]4[N:12]=3)[C@H:5]2[O:4][CH2:3]1.OS([O-])(=O)=O.[K+].[OH-].[Na+].Cl>C(O)=O.C(OCC)(=O)C.O1CCCC1>[OH:1][C@H:2]1[C@H:6]2[O:7][CH2:8][C@@H:9]([O:10][C:11]3[NH:39][C:14]4=[N:15][C:16]([C:20]5[CH:25]=[CH:24][C:23]([C:26]6[CH:27]=[CH:28][C:29]([N:32]=[S:33]([CH3:38])([N:35]([CH3:36])[CH3:37])=[O:34])=[CH:30][CH:31]=6)=[CH:22][CH:21]=5)=[C:17]([Cl:19])[CH:18]=[C:13]4[N:12]=3)[C@H:5]2[O:4][CH2:3]1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 131736735N'-{4-[4-(2-{[(3R,3aR,6R,6aR)-6-Hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]phenyl}-N,N-dimethyl-methanesulfonimidamide

생성물 1

HCID 178486084HCID 178486084, 화합물

시약·촉매·용매 3

HCID 284Formic Acid용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A mixture of N′-{4-[4-(2-{[(3R,3aR,6R,6aR)-6-hydroxy-hexahydrofuro[3,2-b]furan-3-yl]oxy}-6-chloro-3-{[2-(trimethylsilyl)ethoxy]methyl}-3H-imidazo[4,5-b]pyridin-5-yl)phenyl]phenyl}-N,N-dimethyl-methanesulfonimidamide (450 mg) and KHSO4 (2 M aqueous solution, 100 μL) in formic acid (2.4 mL) is stirred for 2 h at 60° C. The mixture is cooled to 0° C. in an ice bath and the pH is adjusted to 11 by adding NaOH (10 M aqueous solution). Tetrahydrofuran (5 mL) is added and the mixture is stirred for 2 h at room temperature. Hydrochloric acid (3 M) is added until the pH reaches 6. The mixture is diluted with ethyl acetate, washed with water and brine, and dried over MgSO4. The solvents are evaporated in vacuo and the residue is chromatographed on silica gel (ethyl acetate/methanol 95:5→80:20) to give the title compound. LC (method 1): tR=0.90 min; Mass spectrum (ESI+): m/z=570 [M+H]+.

후처리

  1. temperatureThe mixture is cooled to 0° C. in an ice bath
  2. stirringthe mixture is stirred for 2 h at room temperature
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvents are evaporated in vacuo
  6. customthe residue is chromatographed on silica gel (ethyl acetate/methanol 95:5→80:20)

출처 및 근거

ORD 기록
ord-54ddee50e670440b921d26b1ea0b36dd
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422312B2

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