p-Toluenesulfonic acid → HCID 66863940, compound

HRID 2093074Notes

Reaction equation

HRID 2093074 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[C:13]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[NH:44][C:45]([C:47]1[S:48][C:49]2[CH2:50][NH:51][CH2:52][CH2:53][C:54]=2[N:55]=1)=[O:46]>ClCCl.CN(C=O)C>[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[NH:44][C:45]([C:47]1[S:48][C:49]2[CH2:50][N:51]([C:1]([O:19][C:16]3[CH:15]=[CH:14][C:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:18][CH:17]=3)=[O:2])[CH2:52][CH2:53][C:54]=2[N:55]=1)=[O:46]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 71034-HydroxybiphenylHCID 682631,1'-CarbonyldiimidazoleHCID 58117006N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Product 1

HCID 66863940HCID 66863940, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (1.0 mmol) was added to biphenyl-4-ol (1.0 mmol) dissolved in of dichloromethane (5.0 mL). Catalytic amount of p-toluenesulphonic acid was added and mixture was stirred at room temperature for 2 to 3 h This solution was then added to N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide obtained from step VIII of example 1 (1.0 mmol) in 10 mL of dry DMF. Reaction mixture was stirred at room temperature overnight. Reaction mixture was concentrated, diluted with water, extracted with dichloromethane washed with brine solution, and dried over anhydrous Na2SO4. Concentrated and purified by column chromatography to yield the title compound.

Workup

  1. customReaction mixture
  2. stirringwas stirred at room temperature overnight
  3. customReaction mixture
  4. concentrationwas concentrated
  5. additiondiluted with water
  6. extractionextracted with dichloromethane
  7. washwashed with brine solution
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationConcentrated
  10. custompurified by column chromatography

Sources & evidence

ORD record
ord-135db0da1dd14891aca2048f8209e91e
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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