Hydrochloric Acid → HCID 178486084、化合物

HRID 1485647ノート

反応式

HRID 1485647 の反応式
[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

参加物

8

反応物 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

生成物 1

HCID 178486084HCID 178486084、化合物

試薬・触媒・溶媒 3

HCID 284Formic Acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-54ddee50e670440b921d26b1ea0b36dd
出典データセット
uspto-grants-2016_08
特許番号
US09422312B2

反応ノート

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