p-Toluenesulfonic acid → HCID 86758134, compound

HRID 2185745Notes

Reaction equation

HRID 2185745 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])[C:3]#[CH: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])[C:3]#[CH:4]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 57233563HCID 57233563, compound

Product 1

HCID 86758134HCID 86758134, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[1-(1,1-dimethyl-2-propynyl)-(2S)-azetidinylmethoxy]-2-fluoropyridine (58 mg, 0.23 mmol) from step 111a above in EtOH (3 mL) was added p-toluenesulfonic acid.monohydrate (44 mg, 0.23 mmol). The solution was stirred for 1 hour, then the volatiles were removed under vacuum. The solid was triturated with Et2O then dried under high vacuum to afford 93 mg (95%) of the the title compound as a white solid: mp 155-157° C.; 1H NMR (D2O) δ1.55 (s, 3H), 1.62 (s, 3H), 2.40 (s, 3H), 2.55 (m, 2H), 3.26 (s, 1H), 4.06 (m, 1H), 4.21 (m, 1H), 4.42 (d, J=4.0 Hz, 2H), 5.05 (m, 1H), 7.10 (dd, J=2.6, 8.8 Hz, 1H), 7.38 (d, J=8.1 Hz, 2H), 7.67 (m, 1H), 7.70 (d, J=8.5 Hz, 2H), 7.91 (m, 1H); MS (CI/NH3) m/z 249 (M+H+). Anal. Calcd for C14H17FN2O.C7H8O3S: C, 59.98; H, 5.99; N, 6.66. Found: C, 59.78; H, 5.91; N, 6.52.

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-07d34fcac1da4be8a7ceb54371ee1332
Source dataset
uspto-grants-2002_06
Patent number
US06403575B1

Reaction notes

Loading…