Dimethylamine, hydrochloride → HCID 86725592, compound

HRID 878628Notes

Reaction equation

HRID 878628 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:9]=[N:10][N:11]([C:22]2[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][N:23]=2)[C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)(=O)=O.Cl.[CH3:31][NH:32][CH3:33].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:31][N:32]([CH3:33])[CH2:6][CH2:7][C:8]1[CH:9]=[N:10][N:11]([C:22]2[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][N:23]=2)[C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 86725593HCID 86725593, compound

Product 1

HCID 86725592HCID 86725592, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[1-(4-cyanopyridin-2-yl)-5-[(4-fluorophenyl)methoxy]pyrazol-4-yl]ethyl methanesulfonate (42 mg, 0.1 mmol) and dimethylamine hydrochloride (41 mg, 0.5 mmol) in ACN (3 mL) was added K2CO3 (276 mg, 2 mmol) and KI (62 mg, 0.4 mmol) at rt. The reaction mixture was heated to 80° C. and stirred overnight. Filtered, solvent removed and purified by prep-HPLC to give the title compound (16 mg, 44%). 1H NMR (400 MHz, CDCl3): δ 2.45 (6H, s), 2.56-2.61 (2H, m), 2.69-2.73 (2H, m), 5.16 (2H, s), 7.03-7.07 (2H, m), 7.35-7.41 (3H, m), 7.53 (1H, s), 8.03 (1H, s), 8.64 (1H, d, J=4.8 Hz). [M+H] Calc'd for C20H20FN5O, 366; Found, 366.

Workup

  1. filtrationFiltered
  2. customsolvent removed
  3. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-3782bf1f15964969a2928d1c4c7b740c
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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