Water → HCID 10248990, compound

HRID 1178704Notes

Reaction equation

HRID 1178704 reaction equation
[SH:1][C:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[S:4][N:3]=1.CCN(C(C)C)C(C)C.[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1.O>CN(C=O)C>[Cl:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][S:1][C:2]2[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([NH:10][C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[S:4][N:3]=2)=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 81531DiisopropylethylamineHCID 178513776HCID 178513776, compound

Product 1

HCID 10248990HCID 10248990, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 14 (50 mg, 0.14 mmol) is dissolved in DMF (0.15 mL) and Hunig's base is added (0.048 mL, 0.27 mmol) followed by 4-chlorobenzyl chloride (22 mg, 0.14 mmol) at room temperature. The reaction is stirred for 1 hour and then water (0.2 mL) is added and the resulting solids are filtered and washed with water and then methylene chloride to provide 3-(4-Chloro-benzylsuIfanyl)-5-(pyridin-3-ylamino)-isothiazole-4-carboxylic acid amide (25.7 mg, 49%). 1H NMR (d6 DMSO): δ 10.37 (1H, br. s), 8.51 (1H, d, J=2.8 Hz), 8.26 (1H, d, J=4.4 Hz), 7.61–7.64 (1H, m), 7.42 (2H, d, J=8 Hz), 7.38–7.41 (1H, m), 7.33 (2H, J=8 Hz), 4.40 (2H, s). LRMS (M+): 376.9, (M−): 374.9.

Workup

  1. filtrationthe resulting solids are filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-25dbb64616aa468b9a2eb9265a066d65
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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