Trifluoroacetic acid methylene chloride → (R)-1-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-3-amine

HRID 339693Notes

Reaction equation

HRID 339693 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([N:20]4[CH2:25][CH2:24][CH2:23][C@@H:22]([NH:26]C(=O)OC(C)(C)C)[CH2:21]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([N:20]4[CH2:25][CH2:24][CH2:23][C@@H:22]([NH2:26])[CH2:21]4)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 67234401(R)-tert-butyl 1-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-3-ylcarbamate

Product 1

HCID 58304331(R)-1-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-3-amineYield 43%

Procedure

(R)-tert-butyl 1-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-3-ylcarbamate (0.030 g, 0.067 mmol) was added to a 1:1 TFA-DCM and stirred for about 2 hours, at which time the reaction appeared complete by LC/TLC. The crude mixture was evaporated and purified by flash column chromatography (Horizon, using a gradient elution of 5% NH4 in MeOH/DCM). The desired product was isolated as a light yellow solid (10 mg; 43% yield). MS ESI (+) m/z 345.2 (M+1) detected.

Workup

  1. customThe crude mixture was evaporated
  2. custompurified by flash column chromatography (Horizon
  3. washa gradient elution of 5% NH4 in MeOH/DCM)

Sources & evidence

ORD record
ord-09ac4f5e9a76466e94b01e148a408f63
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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