Trifluoroacetic acid → HCID 58546859, compound

HRID 1850356Notes

Reaction equation

HRID 1850356 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:14][CH:13]([C:15]2[C:16]([C:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH:22]=3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:12]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:24]1[CH2:23][CH:22]=[C:21]([C:16]2[C:15]([CH:13]3[CH2:12][N:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)[CH2:14]3)=[N:20][CH:19]=[CH:18][N:17]=2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58546905HCID 58546905, compound

Product 1

HCID 58546859HCID 58546859, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 4-(3-(1-(quinolin-2-yl)azetidin-3-yl)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.100 g, 0.225 mmol, SCHEME 5) CH2Cl2 (1 mL) and TFA (0.174 mL, 2.255 mmol) was stirred at RT for 1 h. LCMS showed the product and no more starting material was present. The mixture was concentrated in vacuo and neutralized with Na2CO3. The mixture was extracted with a mixture of CHCl3:i-PrOH (3:1) three times. The organic layer was dried over Na2SO4 and concentrated in vacuo. The product was obtained as a white solid (77 mg, 99%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionThe mixture was extracted with a mixture of CHCl3:i-PrOH (3:1) three times
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ed79187df134a138a46dfa308b8320d
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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