Morpholine → HCID 71270783, compound

HRID 510388Notes

Reaction equation

HRID 510388 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[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.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C(O)C>[CH3:24][C:10]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[C:14]=2[CH3:23])=[C:4]2[N:3]=[C:2]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:7]=[C:6]([NH2:8])[N:5]2[N:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86724877HCID 86724877, compound

Product 1

HCID 71270783HCID 71270783, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 5-chloro-2-methyl-3-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}pyrazolo[1,5-a]pyrimidin-7-amine (331 mg, 0.93 mmol) in ethanol (2 mL) was added morpholine (406 mg, 4.7 mmol). Reaction mixture was heated in microwave reactor at 140° C. for 7 hours. Reaction mixture was concentrated to dryness. It was diluted with ethyl acetate (30 mL) and 5% HCl solution (5 mL). Two layers were separated. Organic layer was dried and concentrated to dryness. Product was obtained and used in next step. (270 mg, 71%); LC/MS: MS (ES+) m/e 406 (MH+).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. concentrationwas concentrated to dryness
  4. additionIt was diluted with ethyl acetate (30 mL) and 5% HCl solution (5 mL)
  5. customTwo layers were separated
  6. customOrganic layer was dried
  7. concentrationconcentrated to dryness
  8. customProduct was obtained

Sources & evidence

ORD record
ord-f582beed4f354a588c7dbb6014f8076f
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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