Hydrochloric Acid → HCID 86670532, compound

HRID 1808747Notes

Reaction equation

HRID 1808747 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[F:23][C:24]([F:36])([F:35])[C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.Cl>CN(C)C1C=CN=CC=1.C(OCC)C.ClCCl>[F:36][C:24]([F:23])([F:35])[C:25]1[CH:26]=[CH:27][C:28]([S:31]([O:1][CH:2]2[CH2:7][CH2:6][N:5]([C:8]3[CH:9]=[CH:10][C:11]([C:14]#[N:15])=[CH:12][N:13]=3)[CH2:4][CH2:3]2)(=[O:33])=[O:32])=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 247031516-(4-hydroxypiperidin-1-yl)pyridine-3-carbonitrile

Product 1

HCID 86670532HCID 86670532, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (50 mL) solution of 6-(4-hydroxypiperidin-1-yl)pyridine-3-carbonitrile (3.19 g, 15.7 mmol) and triethylamine (9.0 mL, 65 mmol) was added 4-(trifluoromethyl)benzenesulfonyl chloride (4.31 g, 17.6 mmol). 4-(Dimethylamino)pyridine (0.19 g, 1.6 mmol) was then added, and the reaction mixture was stirred at room temperature for 2 hours. Diethyl ether (100 mL) was added, followed by 1.0 M hydrochloric acid (70 ml, 70.0 mmol). The organic layer was separated and washed with 1.0 M hydrochloric acid (2×50 mL), saturated brine, dried (magnesium sulfate) to afford the title compound as a solid. This crude product was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 8.39 (d, J=2.3 Hz, 1H), 8.08 (d, J=8.3 Hz, 2H), 7.85 (d, J=8.2 Hz, 2H), 7.61 (dd, J=9.0, 2.4 Hz, 1H), 6.61 (d, J=9.1 Hz, 1H), 4.94-4.88 (m, 1H), 3.87 (ddd, J=13.7, 7.9, 3.8 Hz, 2H), 3.62 (ddd, J=13.8, 7.3, 3.9 Hz, 2H), 1.97-1.90 (m, 2H), 1.89-1.81 (m, 2H); LC-MS: m/z 412.0 (M+H).

Workup

  1. customThe organic layer was separated
  2. washwashed with 1.0 M hydrochloric acid (2×50 mL), saturated brine
  3. dry with materialdried (magnesium sulfate)

Sources & evidence

ORD record
ord-1f62564d8cd9444ca5495b58a9014e28
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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