Trifluoroacetic acid → HCID 67083935, compound

HRID 2239509Notes

Reaction equation

HRID 2239509 reaction equation
[C:1]([C:4]1[N:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[F:22])=[CH:11][C:10]([C:23]1[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH:24]=1)=[C:9]([O:36][CH3:37])[CH:8]=2)(=[O:3])[NH2:2].FC(F)(F)C(O)=O>C(Cl)Cl>[F:22][C:16]1[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=1[NH:14][C:13]1[C:12]2[C:7](=[CH:8][C:9]([O:36][CH3:37])=[C:10]([C:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH:24]=3)[CH:11]=2)[N:6]=[N:5][C:4]=1[C:1]([NH2:2])=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67104624HCID 67104624, compound

Product 1

HCID 67083935HCID 67083935, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(3-carbamoyl-4-(2-fluoro-4-methylphenylamino)-7-methoxycinnolin-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (Example 53, 1.5 g, 2.96 mmol) in CH2Cl2 (11.84 mL) and trifluoroacetic acid (11.84 mL, 153.68 mmol) was stirred for 16 hours, concentrated under reduced pressure, and the residue purified with silica chromatography CH2Cl2/5% MeOH (1% NH4OH) to give 960 mg (80%) product. m/z 408.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue purified with silica chromatography CH2Cl2/5% MeOH (1% NH4OH)

Sources & evidence

ORD record
ord-cfbdbd09573d4723916163e6f0f6e037
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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