Hydrochloric Acid → HCID 70983850, compound

HRID 338869Notes

Reaction equation

HRID 338869 reaction equation
[F:1][C:2]([F:43])([F:42])[CH:3]([N:29]1[CH2:33][CH2:32][C@H:31]([NH:34]C(=O)OC(C)(C)C)[CH2:30]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([NH:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:18][CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1.Cl>C(Cl)(Cl)Cl>[NH2:34][C@H:31]1[CH2:32][CH2:33][N:29]([CH:3]([C:4]2[CH:5]=[CH:6][C:7]3[N:8]([C:10]([C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][C:17]([NH:23][C:24](=[O:28])[CH:25]([CH3:26])[CH3:27])=[CH:18][CH:19]=5)[N:14]=4)=[N:11][N:12]=3)[CH:9]=2)[C:2]([F:43])([F:42])[F:1])[CH2:30]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86707423HCID 86707423, compound

Product 1

HCID 70983850HCID 70983850, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

tert-Butyl (3S)-1-(2,2,2-trifluoro-1-(3-(7-isobutyramido quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (56 mg, 0.094 mmol) was weighed into a 100 mL 1 neck round bottom flask, and dissolve in 5 mL of chloroform, followed by addition of HCl (937 μL, 3.7 mmol). The reaction was then allowed to stir at ambient temperature for 1 hour, at which time the deprotection was complete and light yellow precipitate formed. The reaction was concentrated under vacuum, affording N-(2-(6-(1-((S)-3-aminopyrrolidin-1-yl)-2,2,2-trifluoroethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-7-yl)isobutyramide (32 mg, 69% yield) as a light yellow semi-solid. LCMS APCI (+) m/z 498.2 (M+H).

Workup

  1. customlight yellow precipitate formed
  2. concentrationThe reaction was concentrated under vacuum

Sources & evidence

ORD record
ord-c863f172ae3e484b9a75bcc5142e6e55
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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