Hydrochloric Acid → HCID 178486084, compound

HRID 1485647Notes

Reaction equation

HRID 1485647 reaction equation
[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

Participants

8

Reactant 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

Product 1

HCID 178486084HCID 178486084, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-54ddee50e670440b921d26b1ea0b36dd
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

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