HCID 53629051, compound → HCID 53629050, compound

HRID 386215Notes

Reaction equation

HRID 386215 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[CH:21][C:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:19]3)[NH:9][C:10]([CH:12]2[CH2:15][CH2:14][CH2:13]2)=O)=[N:4][CH:5]=[CH:6][N:7]=1>O=P(Cl)(Cl)Cl>[Cl:1][CH:2]1[NH:7][CH:6]=[CH:5][N:4]2[C:10]([CH:12]3[CH2:15][CH2:14][CH2:13]3)=[N:9][C:8]([C:16]3[CH:17]=[C:18]4[C:23]([N:22]=[CH:21][C:20]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)=[N:19]4)=[CH:24][CH:25]=3)=[C:3]12

Participants

3

Reactant 1

HCID 53629051HCID 53629051, compound

Product 1

HCID 53629050HCID 53629050, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

N-[(3-chloropyrazin-2-yl)(3-phenylquinoxalin-6-yl)methyl]-cyclobutanecarboxamide (56 mg, 0.13 mmol) was heated in POCl3 (5 mL) under Ar at 70° C. for 26 h. Later the reaction was cooled to rt, evaporated under reduced pressure and then high vacuum. A solution of NH3 in i-PrOH (2 M, 10 mL was added to the crude material cooled in an ice-H2O bath under Ar. The mixture was stirred, sonicated and filtered. The solids and the reaction flask were washed with i-PrOH multiple times. The filtrate was concentrated under reduced pressure. The light yellow residue was partitioned between DCM (60 mL) and H2O (20 mL). The aq. layer was extracted with DCM (2×). Combined organic phase was washed with brine and dried (Na2SO4) to afford the title compound as a light yellow solid; 1H NMR (400 MHz, CD3CN) δ 9.40 (s, 1H), 8.36 (s, 1H), 8.32-8.25 (m, 2H), 8.13-8.11 (m, 2H), 7.77 (d, J=4.8 Hz, 1H), 7.63-7.51 (m, 3H), 7.32 (d, J=4.8 Hz, 1H), 3.97 (qund, J=1.2 Hz, 8.4 Hz, 1H), 2.60-2.45 (m, 4H), 2.05-1.95 (m, 2H). MS (ES+): m/z 412.0 (40) [MH+]; HPLC: tR=4.10 min (OpenLynx, polar—5 min).

Workup

  1. customevaporated under reduced pressure
  2. additionA solution of NH3 in i-PrOH (2 M, 10 mL was added to the crude material
  3. temperaturecooled in an ice-H2O bath under Ar
  4. customsonicated
  5. filtrationfiltered
  6. washThe solids and the reaction flask were washed with i-PrOH multiple times
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe light yellow residue was partitioned between DCM (60 mL) and H2O (20 mL)
  9. extractionThe aq. layer was extracted with DCM (2×)
  10. washCombined organic phase was washed with brine
  11. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-e34221cb504a4cffbb640b852291bc20
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

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