HCID 86707503, compound → HCID 136338077, compound

HRID 338990Notes

Reaction equation

HRID 338990 reaction equation
[ClH:1].C1(C[O:6][C:7]2[CH:8]=[C:9]([F:37])[CH:10]=[C:11]3[C:16]=2[N:15]=[C:14]([C:17]2[N:21]4[CH:22]=[C:23]([C@@H:26]([N:31]5[CH2:35][CH2:34][C@H:33]([NH2:36])[CH2:32]5)[C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:25][C:20]4=[N:19][N:18]=2)[CH:13]=[CH:12]3)CC1>Cl.CC(O)C>[ClH:1].[NH2:36][C@H:33]1[CH2:34][CH2:35][N:31]([C@H:26]([C:23]2[CH:24]=[CH:25][C:20]3[N:21]([C:17]([C:14]4[CH:13]=[CH:12][C:11]5[C:16](=[C:7]([OH:6])[CH:8]=[C:9]([F:37])[CH:10]=5)[N:15]=4)=[N:18][N:19]=3)[CH:22]=2)[C:27]([F:29])([F:28])[F:30])[CH2:32]1

Participants

4

Reactant 1

HCID 86707503HCID 86707503, compound

Product 1

HCID 136338077HCID 136338077, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

(S)-1-((R)-1-(3-(8-(cyclopropylmethoxy)-6-fluoroquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-amine hydrochloride (Example 158; 200 mg, 0.400 mmol) was stirred in 5-6N HCl (2 mL) in IPA in a sealed tube at 60° C. for 14 hours. The reaction mixture was concentrated under reduced pressure to provide 2-(6-((R)-1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol hydrochloride (128 mg, 71.8% yield) as a solid. LCMS APCI (+) m/z 447 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cbd9361d0dad40ba84366a1c0686cb6f
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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