O-Methylhydroxylamine hydrochloride → HCID 72448485, compound

HRID 1623109Notes

Reaction equation

HRID 1623109 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[NH2:5][C:6]1[C:11]2[N:12]=[C:13]([CH2:21][CH2:22][CH3:23])[N:14]([CH2:15][CH2:16][CH2:17][C:18](=O)[CH3:19])[C:10]=2[C:9]([CH3:24])=[C:8]([CH3:25])[N:7]=1>CO>[CH3:3][O:2][N:4]=[C:18]([CH2:17][CH2:16][CH2:15][N:14]1[C:10]2[C:9]([CH3:24])=[C:8]([CH3:25])[N:7]=[C:6]([NH2:5])[C:11]=2[N:12]=[C:13]1[CH2:21][CH2:22][CH3:23])[CH3:19]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 58837336HCID 58837336, compound

Product 1

HCID 72448485HCID 72448485, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methoxylamine hydrochloride (0.57 g, 6.8 mmol) was added to a solution of 5-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridine-1-yl)pentan-2-one (1.31 g, 4.5 mmol) in methanol (30 mL) and stirred for 15 minutes. The reaction mixture was concentrated under reduced pressure, dissolved in dichloromethane (150 mL), washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate and concentrated under reduced pressure to afford 1.33 g of crude material. The crude material was purified by HPFC (silca gel, CMA 0-40% in chloroform) and dried overnight at 70° C. at 28 psi (1.9×105 Pa) to afford 0.75 g of 5-(4-amino-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridine-1-yl)pentan-2-one O-methyloxime as an off-white powder, mp 144.0-145.5° C. 1H NMR (300 MHz, DMSO-d6) δ 5.58 (s, 2H), 4.23 (t, J=8.1 Hz, 2H), 3.74 (s, H), 3.71 (s, H), 2.77 (t, J=7.5 Hz, 2H), 2.36 (s, 3H), 2.30 (s, 3H), 2.25 (t, J=7.5 Hz, 2H), 1.80 (m, J=7.5 Hz, 8H), 1.00 (t, J=6.9 Hz, 3H; MS (APCI) m/z 318 (M+H)+; Anal. calcd for C20H26N6O2: C, 64.32; H, 8.57; N, 22.06. Found: C, 64.19; H, 8.86; N, 22.32.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in dichloromethane (150 mL)
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford 1.33 g of crude material
  7. customThe crude material was purified by HPFC (silca gel, CMA 0-40% in chloroform)
  8. customdried overnight at 70° C. at 28 psi (1.9×105 Pa)

Sources & evidence

ORD record
ord-aac6f53cb651493fb6ad6273e8c7ac07
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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