Hydrochloric Acid → HCID 66914201, compound

HRID 2104604Notes

Reaction equation

HRID 2104604 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][C:8]=2[C:21]([OH:23])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1.CCN=C=NCCCN(C)C.Cl.Cl>CN(C1C=CN=CC=1)C.ClCCCl>[CH3:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:21]([C:8]2[CH:9]=[N:10][C:11]3[C:16]([C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]([F:18])([F:19])[F:20])=[O:23])=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66913233HCID 66913233, compound

Product 1

HCID 66914201HCID 66914201, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

4-Phenyl-8-trifluoromethyl-quinoline-3-carboxylic acid (0.110 g, 0.347 mmol), whose preparation is described in Scheme 2, p-toluidine (0.074 mL, 0.693 mmol), EDCI-HCl (0.110 g, 0.520 mmol), and DMAP (0.084 g, 0.520 mmol). are dissolved in 1,2-dichloroethane (3 mL) in a 5 mL microwave tube. After stirring in the microwave reactor for 6 min at 70° C. the cooled solution is poured into 2 N aq HCl and extracted with methylene chloride, washed with water, brine, and dried with magnesium sulfate. The combined extracts are concentrated and the residue is chromatographed in 1:9 ethyl acetate:hexanes to afford the title amide as a white solid (0.078 g, 56%). mp 203-205° C.; MS (ES) m/z 405.2; HRMS: calcd for C24H17N2F3O+H, 407.13712; found (ESI, [M+H]+), 407.1376.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with water, brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe combined extracts are concentrated
  5. customthe residue is chromatographed in 1:9 ethyl acetate

Sources & evidence

ORD record
ord-7592de85abf44176acc3c47c6536e04c
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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