Quinoline → HCID 57882321, compound

HRID 1817367Notes

Reaction equation

HRID 1817367 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:20])[C:10](=[O:19])[NH:11][C:12]=2C(O)=O)[C:7]1=[O:21].N1C2C(=CC=CC=2)C=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:20])[C:10](=[O:19])[NH:11][CH:12]=2)[C:7]1=[O:21]

Participants

3

Reactant 2

HCID 7047QuinolineHCID 59843493HCID 59843493, compound

Product 1

HCID 57882321HCID 57882321, compound

Conditions

Temperature
190 °C

Procedure

A mixture of 6-(3-chloro-4-fluorobenzyl)-4-hydroxy-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxylic acid (0.30 g, 0.82 mmol) and quinoline (0.11 g, 0.82 mmol) was heated at 190° C. for 2.5 hours. The product mixture was cooled to room temperature and triturated with diethyl ether. The solid precipitated was filtered, and was subjected to preparative reverse phase HPLC purification. Collection and lyophilization of appropriate fractions provide the titled compound.

Workup

  1. temperatureThe product mixture was cooled to room temperature
  2. customtriturated with diethyl ether
  3. customThe solid precipitated
  4. filtrationwas filtered
  5. customwas subjected to preparative reverse phase HPLC purification
  6. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-a928109755ab4f13b09237c85486a114
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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