Morpholine → HCID 71272706, compound

HRID 510412Notes

Reaction equation

HRID 510412 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]2[N:9]=[C:10]([CH3:23])[C:11]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[C:4]2[N:3]=1.[OH-].[NH4+:25].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>O1CCOCC1.C(O)C>[CH3:23][C:10]1[C:11]([CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)=[C:4]2[N:3]=[C:2]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:7]=[C:6]([NH2:25])[N:5]2[N:9]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 14923Ammonium HydroxideHCID 86724881HCID 86724881, compound

Product 1

HCID 71272706HCID 71272706, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To the solution of 5,7-dichloro-2-methyl-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidine (0.05 g, 0.146 mmol) in 1,4-Dioxane (5 mL) was added ammonium hydroxide (0.508 mL, 3.65 mmol). The reaction was stirred at rt for 3 days. The reaction was concentrated to give the solid. To the mixture of the solid in Ethanol (1 mL) was added morpholine (0.382 mL, 4.38 mmol). The mixture was subjected to MW irradiation at 150° C. for 6 h. The reaction mixture was concentrated. The crude was purified by reversed phase HPLC (20˜50% CH3CN (0.1% TFA)/Water (0.1% TFA)). The fractions from purification were concentrated. NaHCO3 solution (3 mL) was added in and extracted with EtOAc (20 mL). The organic phase was washed with Brine (5 mL), dried (MgSO4) and concentrated to give the product as solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.18 (s, 3H) 3.46-3.52 (t, J=5.24 Hz, 4H) 3.65-3.74 (t, J=4.52 Hz, 3H) 4.28 (s, 2H) 5.49 (s, 1H) 7.07 (br. s., 2H) 7.31 (m, 1H) 7.37-7.43 (m, 1H) 7.45-7.52 (m, 2H) 7.75 (d, J=8.34 Hz, 1H) 7.85-7.93 (m, 1H) 8.54 (m, 1H); LC/MS: MS (ES+) m/e 374.0 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. customto give the solid
  3. customThe mixture was subjected to MW irradiation at 150° C. for 6 h
  4. concentrationThe reaction mixture was concentrated
  5. customThe crude was purified by reversed phase HPLC (20˜50% CH3CN (0.1% TFA)/Water (0.1% TFA))
  6. customThe fractions from purification
  7. concentrationwere concentrated
  8. additionNaHCO3 solution (3 mL) was added in and
  9. extractionextracted with EtOAc (20 mL)
  10. washThe organic phase was washed with Brine (5 mL)
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-a30f4d685e7a4089aa2ff18cdbfdf9d5
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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