Benzoyl chloride → HCID 58869112, compound

HRID 1623098Notes

Reaction equation

HRID 1623098 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](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>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:39])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[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 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86612245HCID 86612245, compound

Product 1

HCID 58869112HCID 58869112, compoundYield 27.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-8 °C

Procedure

Triethylamine (0.32 mL, 2.29 mmol, 1.2 eq) was added to a solution of 1-[4-(methoxyamino)butyl]-2-propyl-1H-imidazo[4,5-c]-1,5-naphthyridin-4-amine (0.626 g, 1.91 mmol, 1.0 eq), prepared as described in Parts A-H of Example 1, in dichloromethane (10 mL) and cooled to −8° C. Benzoyl chloride (0.22 mL, 1.91 mmol, 1.0 eq) was added dropwise and the reaction mixture was stirred for 2 hours. The reaction was then diluted with dichloromethane (80 mL) and saturated aqueous sodium bicarbonate (40 mL). The phases were separated and the aqueous phase was extracted with dichloromethane (30 mL). The combined organics were dried over magnesium sulfate, filtered, concentrated, and purified by HPFC (silica gel eluting with 0-25% CMA in chloroform) to afford 0.47 g of a pale yellow substance. The material was dissolved in acetonitrile, sonicated, filtered, and dried under vacuum at 100° C. for 24 hours to afford 0.225 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)butyl]-N-methoxybenzamide as off-white needles, mp 125-127° C. Anal. calcd for C24H28N6O2: C, 66.65; H, 6.53; N, 19.43. Found: C, 66.43; H, 6.47; N, 19.60.

Workup

  1. customprepared
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (30 mL)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by HPFC (silica gel eluting with 0-25% CMA in chloroform)
  8. customto afford 0.47 g of a pale yellow substance
  9. customsonicated
  10. filtrationfiltered
  11. customdried under vacuum at 100° C. for 24 hours

Sources & evidence

ORD record
ord-64b30d908ede4b63a0c21afe7964ded6
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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