Acetyl chloride → HCID 59619777, compound

HRID 445769Notes

Reaction equation

HRID 445769 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:16]3[N:15]=[CH:14][C:13]4[N:19]([CH3:30])[C:20](=[O:29])[N:21]([C:22]5[C:23]([CH3:28])=[N:24][N:25]([CH3:27])[CH:26]=5)[C:12]=4[C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1.CCN(C(C)C)C(C)C.[C:40](Cl)(=[O:42])[CH3:41]>ClCCl>[CH3:27][N:25]1[CH:26]=[C:22]([N:21]2[C:12]3[C:11]4[CH:10]=[C:9]([C:5]5[CH:4]=[C:3]([CH2:2][NH:1][C:40](=[O:42])[CH3:41])[CH:8]=[N:7][CH:6]=5)[CH:18]=[CH:17][C:16]=4[N:15]=[CH:14][C:13]=3[N:19]([CH3:30])[C:20]2=[O:29])[C:23]([CH3:28])=[N:24]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 59620031HCID 59620031, compound

Product 1

HCID 59619777HCID 59619777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-(5-aminomethyl-pyridin-3-yl)-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Example 230, 0.053 mmol) and Hünig's base (0.014 ml) in dichloromethane (1 ml) was added acetyl chloride (Aldrich, Buchs, Switzerland, 0.058 mmol). The RM was stirred for 45 min at it then evaporated to dryness. The residue was taken in MeOH and purified by preparative HPLC. The fractions containing product were basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a white solid. (HPLC: tR 1.95 min (Method A); M+H=442 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.99 (s, 1H), 8.56-8.53 (m, 1H), 8.48-8.46 (m, 1H), 8.40 (t, 1H), 8.16-8.12 (m, 2H), 7.94-7.90 (m, 1H), 7.78-7.75 (m, 1H), 7.58-7.56 (m, 1H), 4.38-4.27 (m, 2H), 3.92 (s, 3H), 3.58 (s, 3H), 1.95 (s, 3H), 1.89 (s, 3H))

Workup

  1. customthen evaporated to dryness
  2. custompurified by preparative HPLC
  3. additionThe fractions containing product
  4. concentrationconcentrated
  5. extractionextracted with dichloromethane (2×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customdried under vacuum

Sources & evidence

ORD record
ord-c93a5c871d3f4139b7a7dd295a0c6e9f
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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