Water → n-(2-Aminophenyl)-5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

HRID 2093058Notes

Reaction equation

HRID 2093058 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[S:12][C:13]2[CH2:14][NH:15][CH2:16][CH2:17][C:18]=2[N:19]=1)=[O:10].[N:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[C:21]=[S:22].O>ClCCl>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[S:12][C:13]2[CH2:14][N:15]([C:21]([NH:20][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[S:22])[CH2:16][CH2:17][C:18]=2[N:19]=1)=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 7673Phenyl IsothiocyanateHCID 58117006N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Product 1

HCID 87183260n-(2-Aminophenyl)-5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide. obtained in step VIII of Example 1 (1 eq) in dichloromethane, a solution of isothiocynato benzene (1 eq) in dichloromethane was added and the reaction was stirred at room temperature for 3 h. Water was added and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the title compound.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto afford crude product, which
  5. customon purification by column chromatography

Sources & evidence

ORD record
ord-8aee5f76cf0a4e73864aff009a987b4e
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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