Hydrochloric Acid → HCID 57780995, compound

HRID 1011226Notes

Reaction equation

HRID 1011226 reaction equation
[Cl:1][C:2]1[CH:41]=[C:40]([O:42][C:43]([F:46])([F:45])[F:44])[CH:39]=[CH:38][C:3]=1[CH2:4][NH:5][C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[C:12]([O:31][CH3:32])[C:13]([N:20]3[CH2:25][CH2:24][CH:23]([C:26]([O:28]CC)=[O:27])[CH2:22][CH2:21]3)=[C:14]([F:19])[CH:15]=2)[N:10]([CH2:33][C:34]([F:37])([F:36])[F:35])[CH:9]=1)=[O:7].[OH-].[Li+].Cl.CS(C)=O>O1CCOCC1>[Cl:1][C:2]1[CH:41]=[C:40]([O:42][C:43]([F:46])([F:44])[F:45])[CH:39]=[CH:38][C:3]=1[CH2:4][NH:5][C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[C:12]([O:31][CH3:32])[C:13]([N:20]3[CH2:21][CH2:22][CH:23]([C:26]([OH:28])=[O:27])[CH2:24][CH2:25]3)=[C:14]([F:19])[CH:15]=2)[N:10]([CH2:33][C:34]([F:37])([F:36])[F:35])[CH:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 3939Lithium HydroxideHCID 57781008HCID 57781008, compound

Product 1

HCID 57780995HCID 57780995, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

40 mg (0.059 mmol) of the compound of Example 3 are dissolved in 2 ml of dioxane, and 293 μl (5 eq.) of a 1M solution of lithium hydroxide are added, and the mixture is stirred at RT until the reaction is complete (2 days). The reaction mixture is acidified with 1N hydrochloric acid, a little DMSO is added, and the entire crude solution is separated by preparative HPLC (method 5). 25 mg (65% of theory) of the title compound are obtained.

Workup

  1. custom(2 days)
  2. customthe entire crude solution is separated by preparative HPLC (method 5)

Sources & evidence

ORD record
ord-dd17736929484222b95276179348d916
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Reaction notes

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