Ammonium Chloride → HCID 57742595, compound

HRID 1809563Notes

Reaction equation

HRID 1809563 reaction equation
COC(=O)CC[S:6][C:7]1[CH:8]=[C:9]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:10]([NH:13][C:14]2[S:18][N:17]=[C:16]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[N:15]=2)=[N:11][CH:12]=1.Cl[C:41]1[CH:46]=[CH:45][N:44]=[C:43]2[CH:47]=[CH:48][S:49][C:42]=12.CC([O-])(C)C.[K+].[NH4+].[Cl-]>CS(C)=O>[O:32]([C:9]1[C:10]([NH:13][C:14]2[S:18][N:17]=[C:16]([CH:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH2:24]3)[N:15]=2)=[N:11][CH:12]=[C:7]([S:6][C:41]2[CH:46]=[CH:45][N:44]=[C:43]3[CH:47]=[CH:48][S:49][C:42]=23)[CH:8]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 112752517-Chlorothieno[3,2-b]pyridineHCID 23665647Potassium tert-butoxideHCID 66995289HCID 66995289, compound

Product 1

HCID 57742595HCID 57742595, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 250 mL flask was charged with tert-butyl 4-(5-(5-(3-methoxy-3-oxopropylthio)-3-phenoxypyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (10 g, 17 mmol), 7-chlorothieno[3,2-b]pyridine (3.6 g, 21 mmol), and DMSO (125 mL). Nitrogen was bubbled vigorously through the solution for 10 minutes. Potassium 2-methylpropan-2-olate (5.9 g, 52 mmol) was added and the reaction was stirred at ambient temperature under nitrogen for 5 hours. The reaction was poured into saturated aqueous NH4Cl and extracted with EtOAc (1×500 mL). The organic layer was washed with water and brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica (50 to 75% EtOAc in hexanes) to afford tert-butyl 4-(5-(3-phenoxy-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (10 g, 92% yield) as a white foam.

Workup

  1. customNitrogen was bubbled vigorously through the solution for 10 minutes
  2. extractionextracted with EtOAc (1×500 mL)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica (50 to 75% EtOAc in hexanes)

Sources & evidence

ORD record
ord-219e5191ba654aa7a786cae6828eaf51
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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