Water → 2-Chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide

HRID 1627358Notes

Reaction equation

HRID 1627358 reaction equation
Cl.[NH2:2][CH2:3][C:4](=[O:19])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH2:17])(=[O:16])=[O:15])=[C:10]([Cl:18])[CH:9]=1)([CH3:7])[CH3:6].CCN(CC)CC.[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[S:36])=[CH:30][C:29]=1[O:37][CH3:38].O>C(Cl)Cl>[Cl:18][C:10]1[CH:9]=[C:8]([C:5]([CH3:7])([C:4](=[O:19])[CH2:3][NH:2][C:35]([NH:34][C:31]2[CH:32]=[CH:33][C:28]([F:27])=[C:29]([O:37][CH3:38])[CH:30]=2)=[S:36])[CH3:6])[CH:13]=[CH:12][C:11]=1[S:14]([NH2:17])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 265982444-Fluoro-3-methoxyphenylisothiocyanateHCID 66740651HCID 66740651, compound

Product 1

HCID 866622522-Chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamideYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred mixture of 4-(4-amino-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide hydrochloride (7.8 g, 23.7 mmol) in DCM (150 mL) was added Et3N (9.9 mL, 71.1 mmol, 3 eq) and 1-fluoro-4-isothiocyanato-2-methoxybenzene (4.35 g, 23.7 mmol). After stirring 2 h, DCM and water were added to the reaction mixture. The organic layer was separated, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography (Hex/EtOAc=1:1 to EtOAc/DCM=1:1) to give 2-chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide (8.6 g, 76%). 1H NMR (400 MHz, CDCl3) δ 8.08 (d, J=8.4 Hz, 1H), 7.80 (s, 1H), 7.43 (d, J=2.0 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.15 (m, 1H), 6.89 (d, J=7.6 Hz, 1H), 6.77 (m, 2H), 5.30 (s, 2H), 4.43 (d, J=4.4 Hz, 2H), 3.91 (s, 3H), 1.59 (s, 6H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by flash column chromatography (Hex/EtOAc=1:1 to EtOAc/DCM=1:1)

Sources & evidence

ORD record
ord-b29c42dce17e48f89bc59fc7e012f336
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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