p-Toluenesulfonic acid → HCID 86758135, compound

HRID 2185746Notes

Reaction equation

HRID 2185746 reaction equation
[CH3:1][C:2]([N:6]1[CH2:9][CH2:8][C@H:7]1[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([F:18])=[N:16][CH:17]=1)([CH3:5])[CH2:3][CH3:4].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1>CCO>[S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)([OH:28])(=[O:27])=[O:26].[CH3:5][C:2]([N:6]1[CH2:9][CH2:8][C@H:7]1[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([F:18])=[N:16][CH:17]=1)([CH3:1])[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54239296HCID 54239296, compound

Product 1

HCID 86758135HCID 86758135, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The free amine (84 mg, 0.33 mmol) from step 111c above was dissolved in EtOH (3 mL) and p-toluenesulfonic acid.monohydrate (63 mg, 0.33 mmol) was added. The solution was stirred for 2 hours, then the volatiles were removed under vacuum. The solid was triturated with Et2O then dried under high vacuum to afford 145 mg (95%) of the the title compound as a white solid: mp 84-86° C.; 1H NMR (D2O) δ0.95 (t, J=7.3 Hz, 3H), 1.31 (s, 3H), 1.37 (s, 3H), 1.68 (m, 2H), 2.40 (s, 3H), 2.54 (q, J=8.6 Hz, 1H), 4.02 (m, 1H), 4.15 (m, 1H), 4.43 (m, 2H), 4.97 (m, 1H), 7.11 (dd, J=2.4, 9.2 Hz, 1H), 7.38 (d, J=7.9 Hz, 2H), 7.67 (m, 1H), 7.70 (d, J=8.6 Hz, 2H), 7.91 (dd, J=1.2, 3.1 Hz, 1H); MS (CI/NH3) m/z 253 (M+H+); Anal. Calcd for C14H21FN2O.1.2 C7H8O3S: C, 58.62; H, 6.72; N, 6.10. Found: C, 58.62; H, 6.81; N, 6.45.

Workup

  1. customthe volatiles were removed under vacuum
  2. customThe solid was triturated with Et2O
  3. customthen dried under high vacuum

Sources & evidence

ORD record
ord-10724bc3c23841b194b7e64248d027de
Source dataset
uspto-grants-2002_06
Patent number
US06403575B1

Reaction notes

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