HCID 67167564, compound → HCID 60890783, compound

HRID 536049Notes

Reaction equation

HRID 536049 reaction equation
[CH3:1][N:2]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH3:28])[CH2:23][C:24]([F:27])([F:26])[F:25])=[C:18]([N+:29]([O-])=O)[CH:17]=1)(=[O:15])=[O:14])C(=O)OCC1C=CC=CC=1>CO.[Pd]>[NH2:29][C:18]1[CH:17]=[C:16]([S:13]([NH:2][CH3:1])(=[O:14])=[O:15])[CH:21]=[CH:20][C:19]=1[N:22]([CH3:28])[CH2:23][C:24]([F:26])([F:25])[F:27]

Participants

4

Reactant 1

HCID 67167564HCID 67167564, compound

Product 1

HCID 60890783HCID 60890783, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of phenylmethyl methyl({4-[methyl(2,2,2-trifluoroethyl)amino]-3-nitrophenyl}sulfonyl)carbamate (539 mg, 1.17 mmol) in MeOH (10 mL) at 25° C. was treated with 10% palladium on carbon (124 mg, 0.117 mmol) and stirred under an atmosphere of hydrogen (balloon) overnight before being filtered through celite. The filtrate was again filtered through a 0.45 micron syringe filter and concentrated to give 3-amino-N-methyl-4-[methyl(2,2,2-trifluoroethyl)amino]benzenesulfonamide (320 mg, 92%) as a brown oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.14-7.20 (m, 2 H), 7.12 (d, J=2.26 Hz, 1 H), 6.95 (dd, J=8.28, 2.26 Hz, 1 H), 5.23 (s, 2 H), 3.82 (q, J=9.87 Hz, 2 H), 2.83 (s, 3 H), 2.39 (d, J=5.02 Hz, 3 H). MS (m/z) 298.0 (M+H+).

Workup

  1. filtrationbefore being filtered through celite
  2. filtrationThe filtrate was again filtered through a 0.45 micron syringe
  3. filtrationfilter
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8ce626888ea94f82b5d92decb7ee85aa
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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