Acetic Anhydride → HCID 86641106, compound

HRID 1809612Notes

Reaction equation

HRID 1809612 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:10]=[C:11]([O:27][C:28]2[CH:35]=[CH:34][C:31]([CH:32]=[O:33])=[CH:30][CH:29]=2)[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:20][N:19]=[C:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[N:17]=1.C(N(CC)CC)C.[C:43](OC(=O)C)(=[O:45])[CH3:44].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:43]([N:24]1[CH2:25][CH2:26][CH:21]([C:18]2[N:17]=[C:16]([NH:15][C:14]3[N:13]=[CH:12][C:11]([O:27][C:28]4[CH:29]=[CH:30][C:31]([CH:32]=[O:33])=[CH:34][CH:35]=4)=[CH:10][C:9]=3[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[S:20][N:19]=2)[CH2:22][CH2:23]1)(=[O:45])[CH3:44]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86641105HCID 86641105, compound

Product 1

HCID 86641106HCID 86641106, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(5-(2-chlorophenylthio)-6-(3-(piperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)pyridin-3-yloxy)benzaldehyde (154 mg, 0.294 mmol) was dissolved in methylene chloride (3 mL) and triethylamine (81.9 μL, 0.588 mmol) and acetic anhydride (33.3 μL, 0.353 mmol) were added. After stirring for 20 minutes, the reaction was poured into saturated aqueous sodium bicarbonate and extracted with methylene chloride. The organic layer was concentrated to afford 4-(6-(3-(1-acetylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-chlorophenylthio)pyridin-3-yloxy)benzaldehyde (161 mg, 0.284 mmol, 96.8% yield).

Workup

  1. extractionextracted with methylene chloride
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-47e2f386cff1435384c3e9ec43cb2920
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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