Hydrochloric Acid → HCID 131732358, compound

HRID 1428373Notes

Reaction equation

HRID 1428373 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([N:13]([CH2:21][C:22]#[CH:23])C(=O)OC(C)(C)C)[C:10]([CH3:24])=[N:9]2)[CH:5]=[N:6][CH:7]=1.[ClH:25]>O1CCOCC1.C(OCC)C>[ClH:25].[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([NH:13][CH2:21][C:22]#[CH:23])[C:10]([CH3:24])=[N:9]2)[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86682241HCID 86682241, compound

Product 1

HCID 131732358HCID 131732358, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-yl(prop-2-ynyl)carbamate (1.03 g, 3.11 mmol) in dioxane (5 mL) was added 4 molar (M) hydrogen chloride (HCl; 3.9 mL, 15.5 mmol) in diethyl ether (Et2O). The mixture was stirred at room temperature for 48 h and the resulting white solid was filtered, washed with Et2O and dried under vacuum to give the title compound as a white solid (741 mg, 89%): mp 167-168° C.; 1H NMR (400 MHz, DMSO d6) δ 8.92-8.85 (m, 1H), 8.42 (d, J=2.5 Hz, 1H), 8.15 (s, 1H), 8.12-8.02 (m, 1H), 3.85 (d, J=2.5 Hz, 2H), 3.27-3.19 (m, 1H), 2.22 (s, 3H); ESIMS m/z 230.4 ([M]+).

Workup

  1. filtrationthe resulting white solid was filtered
  2. washwashed with Et2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-178d8affee5e4e6d93c370415bb9837b
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

Loading…