p-Toluenesulfonic acid monohydrate → HCID 86650660, compound

HRID 1969462Notes

Reaction equation

HRID 1969462 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][C:14]([NH2:26])([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=1)[CH3:15]>C(OC)(C)(C)C>[CH3:12][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:15][C:14]([NH2:26])([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[N:17]=1)[CH3:13]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 573469902-[6-(Trifluoromethyl)pyridin-2-yl]propan-2-amine

Product 1

HCID 86650660HCID 86650660, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent3×

Procedure

Add a solution of p-toluenesulfonic acid monohydrate (3.07 g, 16.1 mmol) in t-butylmethyl ether (25 mL) at 40° C. to a solution of 1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamine (3.20 g, 15.7 mmol) in t-butylmethyl ether (15 mL) at 35° C. Allow to cool to ambient temperature, and then add t-butylmethyl ether (10 mL). Stir at ambient temperature for approximately 1 hr. Filter and dry the resulting solid under vacuum at 40° C. to afford the title compound as an off white solid (5.17 g, 88%). 1H NMR (500 MHz, DMSO-d6) δ 8.42 (s, 3H), 8.22 (t, J=8.0 Hz, 1H), 7.98 (d, J=8.0 Hz, 1H), 7.93 (d, J=8.0 Hz, 1H), 7.46 (d, J=8.3 Hz, 2H), 7.10 (d, J=8.3 Hz, 2H), 2.27 (s, 3H), 1.63 (s, 6H).

Workup

  1. filtrationFilter
  2. customdry the resulting solid under vacuum at 40° C.

Sources & evidence

ORD record
ord-9ecf25d6c52a49259d0c0c0214498a76
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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