Sodium Acetate → HCID 178461720, compound

HRID 1046423Notes

Reaction equation

HRID 1046423 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].Cl[C:9]1[N:14]=[N:13][C:12]([O:15][CH2:16][CH2:17][C@@H:18]([N:20]([C:35]([C@H:37]2[CH2:42][CH2:41][C@H:40]([CH3:43])[CH2:39][CH2:38]2)=[O:36])[C:21]2[CH:25]=[C:24]([C:26]#[C:27][C:28]([CH3:31])([CH3:30])[CH3:29])[S:23][C:22]=2[C:32]([OH:34])=[O:33])[CH3:19])=[CH:11][CH:10]=1.CC([O-])=[O:46].[Na+]>CC(O)=O.CO>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[CH3:29][C:28]([CH3:31])([CH3:30])[C:27]#[C:26][C:24]1[S:23][C:22]([C:32]([OH:34])=[O:33])=[C:21]([N:20]([C@@H:18]([CH3:19])[CH2:17][CH2:16][O:15][C:12]2[N:13]=[N:14][C:9]([OH:46])=[CH:10][CH:11]=2)[C:35]([C@H:37]2[CH2:42][CH2:41][C@H:40]([CH3:43])[CH2:39][CH2:38]2)=[O:36])[CH:25]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 178461719HCID 178461719, compound

Product 1

HCID 178461720HCID 178461720, compoundYield 128.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 3-[[3-(6-chloro-pyridazin-3-yloxy)-1(S)-methyl-propyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid TFA salt (0.56 g, 0.087 mmol) in AcOH (2.0 mL) and NaOAc (0.37 g, 0.434 mmol) was placed in a preheated 100° C. oil bath and stirred for 3 h. The reaction was determined to be complete by LC/MS. After cooling, the reaction was diluted with CH3OH (5 mL). 5-(3,3-Dimethyl-but-1-ynyl)-3-[[3-(6-hydroxy-pyridazin-3-yloxy)-1-(S)-methyl-propyl]-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid TFA salt (0.07 g, 13%) was isolated by reverse phase HPLC as an off-white solid.

Workup

  1. customwas placed in a preheated 100° C.
  2. temperatureAfter cooling

Sources & evidence

ORD record
ord-725606087f5d47829874aa49201f59b5
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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