Triethylamine → HCID 58190556, compound

HRID 1959655Notes

Reaction equation

HRID 1959655 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][C:13]1[N:17]2[N:18]=[C:19]([C:22](=O)[CH3:23])[CH:20]=[CH:21][C:16]2=[N:15][CH:14]=1.Cl.[CH2:26]([O:28][NH2:29])[CH3:27].C(N(CC)CC)C>CO>[CH2:26]([O:28]/[N:29]=[C:22](/[C:19]1[CH:20]=[CH:21][C:16]2[N:17]([C:13]([CH2:12][C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][C:2]=3[F:1])[N:9]=[CH:8][CH:7]=[CH:6]4)=[CH:14][N:15]=2)[N:18]=1)\[CH3:23])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76850O-ethylhydroxylamine hydrochlorideHCID 581905991-[3-(7-Fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]ethanone

Product 1

HCID 58190556HCID 58190556, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[3-(7-fluoro-quinolin-6-ylmethyl)-imidazo[1,2-b]pyridazin-6-yl]-ethanone (50 mg, 0.16 mmol) in methanol (10 mL) was added O-ethylhydroxylamine hydrochloride (46 mg, 0.47 mmol). Triethyl amine was added dropwise to adjust the pH to 5-6. The reaction mixture was stirred at rt overnight. The solution was concentrated under reduced pressure and the residue was purified by prep-HPLC to afford 30 mg (53%) of the title compound as a white solid. 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.82 (dd, 1H), 8.30 (d, 1H), 7.93 (m, 2H), 7.85 (d, 1H), 7.70 (d, 1H), 7.66 (s, 1H), 7.49 (q, 1H), 4.62 (s, 2H), 4.31 (q, 2H), 2.27 (s, 3H), 1.36 (t, 3H). LCMS (method C): [MH]+=364, tR=4.71 min.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-4ca22c4db9d34f6db1f3a369d672827a
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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