HCID 86707543, compound → HCID 71004867, compound

HRID 339058Notes

Reaction equation

HRID 339058 reaction equation
[CH2:1]([S:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[N:18]3[CH:19]=[C:20]([C@@H:23]([N:28]4[CH2:32][CH2:31][C@H:30]([NH:33]C(=O)OC(C)(C)C)[CH2:29]4)[C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:22][C:17]3=[N:16][N:15]=1)[CH:10]=[CH:9]2)[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([S:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([C:14]1[N:18]3[CH:19]=[C:20]([C@@H:23]([N:28]4[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29]4)[C:24]([F:26])([F:25])[F:27])[CH:21]=[CH:22][C:17]3=[N:16][N:15]=1)[CH:10]=[CH:9]2)[CH3:2]

Participants

3

Reactant 1

HCID 86707543HCID 86707543, compound

Product 1

HCID 71004867HCID 71004867, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl (S)-1-((R)-1-(3-(8-(ethylthio)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (55 mg, 0.096 mmol) was stirred in TFA for 30 minutes. The reaction was concentrated to dryness, and the residue was diluted in 1 mL of methanol and added dropwise into 4N HCl in ether. The resulting precipitate was filtered and dried under vacuum to yield (S)-1-((R)-1-(3-(8-(ethylthio)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-amine (16 mg, 35% yield) hydrochloride as a solid. LCMS APCI (+) m/z 473 (M+H).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. additionthe residue was diluted in 1 mL of methanol
  3. additionadded dropwise into 4N HCl in ether
  4. filtrationThe resulting precipitate was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-8822426d1065433a9bcae8a9116a45ae
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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