Trifluoroacetic acid → 4-(2-Fluoro-4-methylphenylamino)-7-methoxy-6-(1,2,3,6-tetrahydropyridin-4-yl)cinnoline-3-carbonitrile

HRID 2239527Notes

Reaction equation

HRID 2239527 reaction equation
[C:1]([C:3]1[N:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[F:21])=[CH:10][C:9]([C:22]1[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH:23]=1)=[C:8]([O:35][CH3:36])[CH:7]=2)#[N:2].FC(F)(F)C(O)=O>C(Cl)Cl>[F:21][C:15]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=1[NH:13][C:12]1[C:11]2[C:6](=[CH:7][C:8]([O:35][CH3:36])=[C:9]([C:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH:23]=3)[CH:10]=2)[N:5]=[N:4][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67084327HCID 67084327, compound

Product 1

HCID 670842344-(2-Fluoro-4-methylphenylamino)-7-methoxy-6-(1,2,3,6-tetrahydropyridin-4-yl)cinnoline-3-carbonitrileYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(3-cyano-4-(2-fluoro-4-methylphenylamino)-7-methoxycinnolin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Method 85, 600 mg, 1.23 mmol) in CH2Cl2 (4.9 mL) and trifluoroacetic acid (4.9 mL, 63.6 mmol) was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure, azeotroped with chloroform to remove trifluoroacetic acid, and the residue purified with reverse phase HPLC (MeCN/water) to give 302 mg (63%) product. m/z 390.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customazeotroped with chloroform
  3. customto remove trifluoroacetic acid
  4. customthe residue purified with reverse phase HPLC (MeCN/water)

Sources & evidence

ORD record
ord-319d87ff38c64fbf9f6f3e1a207e9bff
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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