Water → HCID 89704808, compound

HRID 928994Notes

Reaction equation

HRID 928994 reaction equation
[NH2:1][C:2]1[C:11]([SH:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[C:3]=1[F:21].[CH3:22]C1C=CC(S(O)(=O)=O)=CC=1.O>C(OC)(OC)OC>[F:21][C:3]1[C:2]2[N:1]=[CH:22][S:12][C:11]=2[CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 89704800HCID 89704800, compound

Product 1

HCID 89704808HCID 89704808, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 9005Trimethyl orthoformateSolvent

Procedure

To a solution of methyl 4-amino-3-fluoro-2-((2-fluorophenyl)amino)-5-mercaptobenzoate in trimethyl orthoformate (50 mL) was added p-TsOH (0.61 g, 3.17 mmol). The reaction mixture was stirred for 1 h and treated with water (100 mL). The precipitate was filtered off and the filter cake was washed with water to afford the desired product (pale yellow solid, 8.64 g, 85.1% yield for two steps). 1H NMR (400 MHz, CDCl3): δ 9.13 (s, 1H), 8.68 (s, 1H), 8.46 (s, 1H), 7.10 (m, 1H), 7.01 (m, 1H), 6.92 (s, 2H), 3.97 (s, 3H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washthe filter cake was washed with water

Sources & evidence

ORD record
ord-6a88660919534373bbaeca9588c60e94
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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