HCID 53983458, compound → HCID 54417386, compound

HRID 1857603Notes

Reaction equation

HRID 1857603 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:33])=[C:24]([NH:27][C:28]([CH:30]3[CH2:32][CH2:31]3)=[O:29])[CH:25]=2)[NH:20][C:19](=[O:34])[C:18]=1[C:35]1[CH:40]=[C:39]([CH3:41])[CH:38]=[C:37]([CH3:42])[CH:36]=1)=O)(C)(C)C>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[Cl:33][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([O:16][CH2:15][CH2:14][CH:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[C:18]([C:35]3[CH:36]=[C:37]([CH3:42])[CH:38]=[C:39]([CH3:41])[CH:40]=3)[C:19](=[O:34])[NH:20]2)=[CH:25][C:24]=1[NH:27][C:28]([CH:30]1[CH2:31][CH2:32]1)=[O:29]

Participants

4

Reactant 1

HCID 53983458HCID 53983458, compound

Product 1

HCID 54417386HCID 54417386, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 2-{2-[7-chloro-6-(cyclopropanecarbonylamino)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (80 mg in a mixture of 8 mL trifluoroacetic acid and 0.03 mL anisole) was stirred at room temperature for 1 hour. The mixture was then concentrated in vacuo, resolvated in methylene chloride and washed with saturated sodium bicarbonate. The concentrated organics were purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 94:3:1) to give the title compound (52 mg). MASS: 494 (M+H)

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. washwashed with saturated sodium bicarbonate
  3. customThe concentrated organics were purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 94:3:1)

Sources & evidence

ORD record
ord-608f26c73b024dbca651b35cea815570
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

Loading…