Hydrochloric Acid → HCID 125484987, compound

HRID 1777942Notes

Reaction equation

HRID 1777942 reaction equation
Cl.COC1C=CC(C[NH:9][C:10]2[CH:15]=[C:14]([NH:16][CH2:17][CH2:18][O:19][CH3:20])[C:13]([C:21]([F:24])([F:23])[F:22])=[CH:12][N:11]=2)=CC=1.C([O-])(O)=O.[Na+]>>[CH3:20][O:19][CH2:18][CH2:17][NH:16][C:14]1[C:13]([C:21]([F:24])([F:22])[F:23])=[CH:12][N:11]=[C:10]([NH2:9])[CH:15]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131734787HCID 131734787, compound2×

Product 1

HCID 125484987HCID 125484987, compound

Procedure

Concentrated hydrochloric acid (1.5 ml) was added to N2-(4-methoxybenzyl)-N4-(2-methoxyethyl)-5-(trifluoromethyl)pyridine-2,4-diamine (intermediate 85, 280 mg, 0.788 mmol) at room temperature. After stirring for 4.5 h the reaction mixture was neutralised with saturated aqueous NaHCO3 solution, extracted with DCM (4×), dried over Na2SO4 and evaporated. The residue was applied to a 12 g RediSep® silica column as a DCM solution and purified by normal phase chromatography, eluting with a gradient from DCM to 10% MeOH in DCM. Product containing fractions were combined and evaporated to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 5.68 (s, 1H), 4.95 (s, br, 1H), 4.50 (s, br, 2H), 3.62-3.57 (m, 2H), 3.38 (s, 3H), 3.30-3.25 (m, 2H). (UPLC-MS 6) tR 0.44; ESI-MS 236.1 [M+H]+.

Workup

  1. extractionextracted with DCM (4×)
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. custompurified by normal phase chromatography
  5. washeluting with a gradient from DCM to 10% MeOH in DCM
  6. additionProduct containing fractions
  7. customevaporated

Sources & evidence

ORD record
ord-e64702875ed0419497411eb1760c1225
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

Loading…