Trifluoroacetic acid → HCID 22284885, compound

HRID 1061517Notes

Reaction equation

HRID 1061517 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[Cl:18])=[CH:15][C:14]([O:19][CH3:20])=[C:13]([O:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH:12]=2)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[NH4+]>ClCCl>[Cl:18][C:17]1[C:16]2[C:11](=[CH:12][C:13]([O:21][CH2:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:14]([O:19][CH3:20])[CH:15]=2)[N:10]=[CH:9][C:8]=1[NH2:7]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 69748021HCID 69748021, compound

Product 1

HCID 22284885HCID 22284885, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4-chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinolin-3-yl]-carbamic acid tert-butylester (1.8 g) was dissolved in dichloromethane and added trifluoroacetic acid (2 ml) and stirred at room temperature for 2 h. This was carefully basified with ammonium hydroxide solution and extracted the desired amino product with ethyl acetate. The solvent was evaporated to give 4-chloro-6-methoxy-7-(3-piperidin-1-yl-propoxy)-quinolin-3-ylamine (0.500 g). MS(ES) 350 (M+H).

Workup

  1. extractionextracted the desired amino product with ethyl acetate
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ed3eebbe0ce1475280fe06241f22d70c
Source dataset
uspto-grants-2005_11
Patent number
US06960580B2

Reaction notes

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