Hydrochloric Acid → HCID 57960940, compound

HRID 449075Notes

Reaction equation

HRID 449075 reaction equation
[CH:1]1([C:5]2[N:9]3[CH:10]=[CH:11][N:12]=[C:13]([NH2:14])[C:8]3=[C:7]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=4)=[CH:17][CH:16]=3)[N:6]=2)[CH2:4][CH2:3][CH2:2]1.CCO.Cl.C([O-])(O)=O.[Na+]>[Fe]>[NH2:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[O:21][C:18]1[CH:19]=[CH:20][C:15]([C:7]2[N:6]=[C:5]([CH:1]3[CH2:2][CH2:3][CH2:4]3)[N:9]3[CH:10]=[CH:11][N:12]=[C:13]([NH2:14])[C:8]=23)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 57961040HCID 57961040, compound

Product 1

HCID 57960940HCID 57960940, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

A mixture of 3-cyclobutyl-1-[4-(3-nitrophenoxy)-phenyl]-imidazo[1,5-a]pyrazin-8-ylamine (10 mg, 0.02 mmol), iron (10 mg, 0.2 mmol), EtOH (10 mL, 0.2 mol) and conc. HCl (100 uL, 0.003 mol) was refluxed for 1 h. Sat. NaHCO3 was added to quench, and the EtOH was removed in vacuo. The mixture was transferred to a separatory funnel, and DCM was used to extract the product. The organic layer was concentrated in vacuo, redissolved in minimal MeOH/DCM, and loaded onto a prep TLC plate. After eluting with 10% (7N NH3 in MeOH)/DCM, the band containing the pure product was collected, and the material filtered off using 1:1 MeOH/DCM. The filtrate was concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=2.00-2.08 (m, 1H) 2.13-2.24 (m, 1H) 2.44-2.55 (m, J=8.91, 8.75, 8.75, 2.91, 2.78 Hz, 2H) 2.64 (quin, J=9.28 Hz, 2H) 3.71 (br. s., 2H) 3.82 (dq, J=8.84, 8.59 Hz, 1H) 5.05 (br. s., 2H) 6.38 (t, J=2.15 Hz, 1H) 6.46 (dd, J=8.08, 1.26 Hz, 2H) 7.05-7.16 (m, 5H) 7.63 (d, J=8.59 Hz, 2H). MS (ES+): m/z 372.10 (20) [MH+]. HPLC: tR=2.22 min (Open Lynx, polar—5 min).

Workup

  1. temperaturewas refluxed for 1 h
  2. customto quench
  3. customthe EtOH was removed in vacuo
  4. customThe mixture was transferred to a separatory funnel
  5. extractionto extract the product
  6. concentrationThe organic layer was concentrated in vacuo
  7. dissolutionredissolved in minimal MeOH/DCM
  8. washAfter eluting with 10% (7N NH3 in MeOH)/DCM
  9. additionthe band containing the pure product
  10. customwas collected
  11. filtrationthe material filtered off
  12. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-39ebbe7b7538495e837c92e3face27d1
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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