Trifluoroacetic acid → (R)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-N-(pyrrolidin-3-yl)quinolin-8-amine

HRID 1095671Notes

Reaction equation

HRID 1095671 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([NH:25][C@H:26]5[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]5)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([NH:25][C@@H:26]5[CH2:30][CH2:29][NH:28][CH2:27]5)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44185162(S)-tert-butyl 3-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ylamino)pyrrolidine-1-carboxylate

Product 1

HCID 24996492(R)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-N-(pyrrolidin-3-yl)quinolin-8-amineYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-tert-butyl 3-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ylamino)pyrrolidine-1-carboxylate (0.127 g, 0.252 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (0.389 ml, 5.04 mmol). The resulting mixture was stirred for 2 hours at ambient temperature. The dichloromethane reaction mixture was concentrated under reduced pressure and then diluted with dichloromethane. The resulting solution was washed twice with saturated sodium bicarbonate and twice with a brine solution. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification via flash column chromatography (40:1 CH2Cl2/MeOH to 20:1 CH2Cl2/MeOH to 10:1 CH2Cl2/MeOH) produced the title compound (53 mg, 52% Yield). MS APCI (+) m/z 404.3 (M+1) detected.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additiondiluted with dichloromethane
  3. washThe resulting solution was washed twice with saturated sodium bicarbonate and twice with a brine solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification via flash column chromatography (40:1 CH2Cl2/MeOH to 20:1 CH2Cl2/MeOH to 10:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-7b36426d066d4c8a91b9c403fd48573d
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

Loading…