Hydrochloric Acid → HCID 45254557, compound

HRID 2065617Notes

Reaction equation

HRID 2065617 reaction equation
C([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[C:11]([Cl:17])[CH:10]=2)=[O:5])C.[NH2:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O>[C:28]([C@@H:20]([NH:19][C:7]1[C:6]([C:4]([OH:3])=[O:5])=[CH:15][C:14]2[C:9](=[CH:10][C:11]([Cl:17])=[C:12]([Cl:16])[CH:13]=2)[N:8]=1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([OH:30])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6140L-PhenylalanineHCID 11430Potassium CarbonateHCID 86656376HCID 86656376, compound

Product 1

HCID 45254557HCID 45254557, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2,6,7-trichloroquinoline-3-carboxylic acid ethyl ester (80 mg, 0.26 mmol), L-phenylalanine (80 mg, 0.52 mmol) and potassium carbonate (180 mg, 1.31 mmol) in DMF (1 mL) is stirred for 22 h at 130° C. in closed reaction vial. After cooling the reaction mixture is diluted with water, acidified by addition of 2N HCl, and the precipitated solid is collected on filter, washed with water and air dried to give the title compound (40 mg, 38%) as yellow powder.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customthe precipitated solid is collected
  3. filtrationon filter
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-15460a8994f74a2682015420d8bac3ee
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

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