Trifluoroacetic acid → HCID 86641105, compound

HRID 1809611Notes

Reaction equation

HRID 1809611 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[C:10]([NH:24][C:25]2[S:29][N:28]=[C:27]([CH:30]3[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]3)[N:26]=2)=[N:11][CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][CH:17]=2)[CH:14]=1.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]=[O:23])=[CH:20][CH:21]=2)[CH:12]=[N:11][C:10]=1[NH:24][C:25]1[S:29][N:28]=[C:27]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[N:26]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86641104HCID 86641104, compound

Product 1

HCID 86641105HCID 86641105, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(5-(3-(2-chlorophenylthio)-5-(4-formylphenoxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (183 mg, 0.293 mmol) was dissolved in methylene chloride (1 mL) and TFA (1 mL) was added. After stirring for 30 minutes, the reaction was poured into saturated aqueous sodium bicarbonate. The mixture was extracted with methylene chloride and concentrated to afford 4-(5-(2-chlorophenylthio)-6-(3-(piperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)pyridin-3-yloxy)benzaldehyde (154 mg, 0.294 mmol).

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-39bc8fef7da443b4bcbe3a2674d357ec
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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