Acetic Anhydride → HCID 11257222, compound

HRID 1623097Notes

Reaction equation

HRID 1623097 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][NH:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:27]2[C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:20]=[C:19]([NH2:28])[C:18]=2[N:17]=[C:16]1[CH2:29][CH2:30][CH3:31].[C:32](OC(=O)C)(=[O:34])[CH3:33]>ClCCl.C(=O)(O)[O-].[Na+].C(#N)C>[NH2:28][C:19]1[C:18]2[N:17]=[C:16]([CH2:29][CH2:30][CH3:31])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][N:10]([O:9][CH3:8])[C:32](=[O:34])[CH3:33])[C:27]=2[C:26]2[N:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 86612245HCID 86612245, compound

Product 1

HCID 11257222HCID 11257222, compoundYield 53.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.24 mL, 1.69 mmol, 1.2 eq) was added to 1-[4-(methoxyamino)butyl]-2-propyl-1H-imidazo[4,5-c]-1,5-naphthyridin-4-amine (0.46 g, 1.41 mmol, 1.0 eq) in dichloromethane (6 mL) and cooled to 0° C. Acetic anhydride (0.13 mL, 1.41 mmol, 1.0 eq) was added dropwise and the reaction mixture was stirred for 1 hour. The reaction was then diluted with dichloromethane (40 mL) and saturated aqueous sodium bicarbonate (30 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (20 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated to afford a yellow solid, which was purified by HPFC (silica gel eluting with 0-25% CMA in chloroform) to afford 0.49 g of a pale yellow substance. The material was dissolved in acetonitrile (10 mL), sonicated for 2 minutes, filtered, and dried under vacuum at 100° C. for 24 hours to afford 0.278 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-N-methoxyacetamide as off-white needles, mp 155-156° C. Anal. calcd for C19H26N6O2: C, 61.60; H, 7.07; N, 22.69. Found: C, 61.58; H, 7.31; N, 22.64.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with dichloromethane (20 mL)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a yellow solid, which
  7. customwas purified by HPFC (silica gel eluting with 0-25% CMA in chloroform)
  8. customto afford 0.49 g of a pale yellow substance
  9. customsonicated for 2 minutes
  10. filtrationfiltered
  11. customdried under vacuum at 100° C. for 24 hours

Sources & evidence

ORD record
ord-ffd0f19d70694d7b808b7c63b2e3c61d
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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