Ammonium Hydroxide → HCID 86724877, compound

HRID 510387Notes

Reaction equation

HRID 510387 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([CH3:24])[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=3[CH3:23])=[C:4]2[N:3]=1.[OH-].[NH4+:26]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:26])[N:5]2[N:9]=[C:10]([CH3:24])[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[C:14]=3[CH3:23])=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86724866HCID 86724866, compound

Product 1

HCID 86724877HCID 86724877, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 5,7-dichloro-2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}pyrazolo[1,5-a]pyrimidine (374 mg, 1.0 mmol), prepared as described in Example 1 step c, and 30% ammonium hydroxide solution (584 mg, 5.0 mmol) in 1,4-dioxane (5 mL) stirred at 20° C. for 30 hours. Reaction mixture was concentrated in vacuo. The residue was dissolved with ethyl acetate (50 mL) and 5 NaHCO3 solution (10 mL). Organic layer was separated, washed with brine (5 mL) and dried. Crude product was purified on silica gel column chromatography (methanol and DCM, 0-10%). Fractions were collected and concentrated to afford the titled product, which was in next step. (331 mg, 93%); LC/MS: MS (ES+) m/e 355 (MH+).

Workup

  1. customprepared
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe residue was dissolved with ethyl acetate (50 mL) and 5 NaHCO3 solution (10 mL)
  5. customOrganic layer was separated
  6. washwashed with brine (5 mL)
  7. customdried
  8. customCrude product was purified on silica gel column chromatography (methanol and DCM, 0-10%)
  9. customFractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-6977a77af00b4b6283543211562c9907
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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