Ethanol, 2-(aminooxy)- → HCID 58190605, compound

HRID 1959755Notes

Reaction equation

HRID 1959755 reaction equation
[C:1]([C:4]1[N:9]=[C:8]2[N:10]([CH2:13][C:14]3[CH:15]=[C:16]4[C:21](=[CH:22][CH:23]=3)[N:20]=[CH:19][C:18]([C:24](=O)[CH3:25])=[CH:17]4)[N:11]=[N:12][C:7]2=[N:6][CH:5]=1)(=O)[CH3:2].[NH2:27][O:28][CH2:29][CH2:30][OH:31]>CO.C(O)(=O)C>[OH:31][CH2:30][CH2:29][O:28]/[N:27]=[C:24](/[C:18]1[CH:19]=[N:20][C:21]2[C:16]([CH:17]=1)=[CH:15][C:14]([CH2:13][N:10]1[C:8]3=[N:9][C:4](/[C:1](=[N:27]/[O:28][CH2:29][CH2:30][OH:31])/[CH3:2])=[CH:5][N:6]=[C:7]3[N:12]=[N:11]1)=[CH:23][CH:22]=2)\[CH3:25]

Participants

5

Reactant 2

HCID 3014186Ethanol, 2-(aminooxy)-HCID 58190565HCID 58190565, compound

Product 1

HCID 58190605HCID 58190605, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1-(6-((6-acetyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinolin-3-yl)ethanone (74 mg, 0.213 mmol) and 2-aminooxy-ethanol (35 mg, 0.45 mmol) in 5 mL of methanol and 0.1 mL of acetic acid was stirred at 40° C. overnight. The solvent was removed under reduced pressure and the residue was diluted with DCM and methanol. The precipitate was collected, washed with DCM, dried to afford the title compound (16 mg, 15%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.31 (s, 1H), 9.23 (d, 1H), 8.52 (d, 1H), 8.03 (d, 1H), 7.98 (s, 1H), 7.86 (dd, 1H), 6.22 (s, 2H), 4.76 (d, 2H), 4.31 (t, 2H), 4.22 (t, 2H), 3.72-3.69 (m, 4H), 2.32 (s, 3H), 2.29 (s, 3H). LCMS (method E): [MH]+=465, tR=4.85 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with DCM and methanol
  3. customThe precipitate was collected
  4. washwashed with DCM
  5. customdried

Sources & evidence

ORD record
ord-bb3548c2ff4c467e88feb350493023c5
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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