Diethylamine → HCID 22914666, compound

HRID 1377720Notes

Reaction equation

HRID 1377720 reaction equation
[CH:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([O:12][C:13]2[CH:37]=[CH:36][C:16]([C:17]([N:19]3[CH2:24][CH2:23][CH:22]([N:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:28][CH2:27][C:26]4=[O:35])[CH2:21][CH2:20]3)=[O:18])=[C:15]([O:38][CH3:39])[CH:14]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])=[CH2:2].[CH2:40]([NH:42][CH2:43][CH3:44])[CH3:41]>CO>[CH2:40]([N:42]([CH2:43][CH3:44])[CH2:2][CH2:1][S:3]([N:6]1[CH2:7][CH2:8][CH:9]([O:12][C:13]2[CH:37]=[CH:36][C:16]([C:17]([N:19]3[CH2:20][CH2:21][CH:22]([N:25]4[C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[CH2:28][CH2:27][C:26]4=[O:35])[CH2:23][CH2:24]3)=[O:18])=[C:15]([O:38][CH3:39])[CH:14]=2)[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:41]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 22914660HCID 22914660, compound

Product 1

HCID 22914666HCID 22914666, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(1-(4-(N-vinylsulfonyl-4-piperidinyloxy)-2-methoxybenzoyl)piperidin-4-yl)-3,4-dihydro-2(1H)-quinolinone (80 mg, 0.14 mmol) from Example 192 in 5 mL of dry MeOH was added diethylamine (0.14 mL, 1.4 mmol) and the reaction stirred at ambient temperature for 16 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 dissolved in EtOAc and the solvent was removed under reduced pressure to give the title compound as an amorphous solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by pressurized silica gel column chromatography
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5ddb5ab39c334341a9b0252ce5ddeb47
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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