Diisopropylethylamine → HCID 22914692, compound

HRID 1377722Notes

Reaction equation

HRID 1377722 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][CH:20]([N:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH2:26][CH2:25][C:24]4=[O:33])[CH2:19][CH2:18]3)=[O:16])=[C:10]([O:34][CH3:35])[CH:9]=2)[CH2:3][CH2:2]1.[CH3:36][C:37]1[C:42]([CH2:43]Cl)=[CH:41][CH:40]=[CH:39][N:38]=1.CCN(C(C)C)C(C)C>>[CH3:43][C:42]1[C:37]([CH2:36][N:1]2[CH2:6][CH2:5][CH:4]([O:7][C:8]3[CH:13]=[CH:12][C:11]([CH2:14][C:15]([N:17]4[CH2:18][CH2:19][CH:20]([N:23]5[C:32]6[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=6)[CH2:26][CH2:25][C:24]5=[O:33])[CH2:21][CH2:22]4)=[O:16])=[C:10]([O:34][CH3:35])[CH:9]=3)[CH2:3][CH2:2]2)=[N:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 122437113-(Chloromethyl)-2-methylpyridineHCID 22914700HCID 22914700, compound

Product 1

HCID 22914692HCID 22914692, compound

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(1-(4-(4-piperidinyloxy)-2-methoxyphenylacetyl)piperidin-4-yl)-3,4-dihydro-2(1H)-quinolinone (200 mg, 0.34 mmol) from Example 195 in dry degassed DMF (5 mL) was added 2-methyl-3-chloromethylpyridine (100 mg, 0.68 mmol) and DIEA (0.10 mL, 0.66 mmol) and the reaction was warmed to 50° C. for 72 hours. The solvent was removed under reduced pressure and the residue was purified by pressurized silica gel column chromatography using 98:2 CH2Cl2 :MeOH as eluant. The product-containing fractions were combined and the solvent was removed under reduced pressure. The residue was lyophilized from acetonitrile-water to give the title compound as an amorphous solid.

Workup

  1. customdegassed DMF (5 mL)
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by pressurized silica gel column chromatography
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3587546e04844bc3b4ed9f7597f6b6c4
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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