Acetic Acid → HCID 86687465, compound

HRID 1473416Notes

Reaction equation

HRID 1473416 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([N:26]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C:27]3[S:28][CH:29]=[CH:30][N:31]=3)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[N:16]=[CH:15][C:14]=1[N+:41]([O-])=O.C(O)(=O)C>C1COCC1.[Fe]>[NH2:41][C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:13]=1[C:4]1[CH:5]=[CH:6][C:7]([C:9]([F:10])([F:11])[F:12])=[CH:8][C:3]=1[O:2][CH3:1])=[CH:21][CH:20]=[C:19]([S:23]([N:26]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=1)[C:27]1[S:28][CH:29]=[CH:30][N:31]=1)(=[O:24])=[O:25])[CH:18]=2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86687463HCID 86687463, compound

Product 1

HCID 86687465HCID 86687465, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A round-bottom flask was charged with 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-3-nitro-N-(thiazol-2-yl)quinoline-7-sulfonamide (0.759 g, 1.204 mmol), THF (2.006 ml), and acetic acid (2.006 ml) to give a yellow solution. Iron (0.672 g, 12.04 mmol) powder was added, and the flask was fitted with a reflux condenser and placed in a 60° C. heating bath. The mixture was stirred for 50 min, then cooled to room temperature, diluted with THF, and filtered through diatomaceous earth with the aid of THF. The filtrate was concentrated. The residue was concentrated from DCM/heptane (2×), then concentrated from DCM to give 3-amino-4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (0.714 g, 1.189 mmol, 99% yield) as a tan foam. m/z (ESI) 601.2 (M+H)+.

Workup

  1. customto give a yellow solution
  2. customthe flask was fitted with a reflux condenser
  3. customplaced in a 60° C.
  4. temperatureheating bath
  5. filtrationfiltered through diatomaceous earth with the aid of THF
  6. concentrationThe filtrate was concentrated
  7. concentrationThe residue was concentrated from DCM/heptane (2×)
  8. concentrationconcentrated from DCM

Sources & evidence

ORD record
ord-e28afc3f0af84646aeceb73bf8bfe093
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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