2-Methylmorpholine → HCID 178429997, compound

HRID 510374Notes

Reaction equation

HRID 510374 reaction equation
Cl[C:2]1[CH:7]=[C:6]([OH:8])[N:5]2[N:9]=[C:10]([C:21]([F:24])([F:23])[F:22])[C:11]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=3[Cl:20])=[C:4]2[N:3]=1.[CH3:25][CH:26]1[O:31][CH2:30][CH2:29][NH:28][CH2:27]1>C(O)C.C(OCC)(=O)C>[Cl:20][C:14]1[C:15]([Cl:19])=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][C:11]1[C:10]([C:21]([F:24])([F:23])[F:22])=[N:9][N:5]2[C:6]([OH:8])=[CH:7][C:2]([N:28]3[CH2:29][CH2:30][O:31][CH:26]([CH3:25])[CH2:27]3)=[N:3][C:4]=12

Participants

5

Reactant 2

HCID 4106152-MethylmorpholineHCID 178516190HCID 178516190, compound

Product 1

HCID 178429997HCID 178429997, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-3-[(2,3-dichlorophenyl)methyl]-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-7-ol (79 mg, 0.2 mmol), prepared as described in Example 7 step b, in ethanol (2 mL) was added 2-methylmorpholine (101 mg, 1.0 mmol) in a microwave reaction vessel. It was sealed and irradiated (microwave) at 150° C. for seven hours. The reaction mixture was diluted with ethyl acetate (20 mL), washed with 5% HCl solution (5 mL). Organic layer was dried, filtered, and concentrated. The crude product was purified by reverse-phase HPLC to provide the titled compound. (17 mg, 18%); LC/MS: MS (ES+) m/e 461 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13 (d, J=6.32 Hz, 3H) 2.68 (m, 1H) 2.96 (m, 1H) 3.56 (m, 2H) 3.71 (m, 2H) 3.88 (m, 1H) 4.20 (s, 2H) 5.23 (s, 1H) 6.85 (s, 1H) 7.25 (t, J=7.96 Hz, 1H) 7.53 (d, J=7.58 Hz, 1H) 11.24 (s, 1H).

Workup

  1. customin a microwave reaction vessel
  2. customIt was sealed
  3. customirradiated (microwave) at 150° C. for seven hours
  4. washwashed with 5% HCl solution (5 mL)
  5. customOrganic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-cf95cda67565455b9e52d3cca3b166b1
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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