Hydrochloric Acid → 2,2-Dimethyl-3-(2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)propan-1-amine trihydrochloride

HRID 876510Notes

Reaction equation

HRID 876510 reaction equation
[CH3:1][C:2]([CH3:34])([CH2:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([C:24]1[N:28]3[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:27]3=[N:26][N:25]=1)[CH:20]=[CH:19]2)[CH2:3][NH:4]C(=O)OC(C)(C)C.[ClH:35]>ClCCl>[ClH:35].[ClH:35].[ClH:35].[CH3:1][C:2]([CH3:34])([CH2:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([C:24]1[N:28]3[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:27]3=[N:26][N:25]=1)[CH:20]=[CH:19]2)[CH2:3][NH2:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67230779Tert-butyl 2,2-dimethyl-3-(2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)propylcarbamate

Product 1

HCID 672331932,2-Dimethyl-3-(2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)propan-1-amine trihydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2,2-dimethyl-3-(2-(7-methyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)propylcarbamate (35 mg, 0.076 mmol) and hydrochloric acid (4 M in dioxane, 0.57 mL, 2.3 mmol) in dichloromethane (0.5 mL) was stirred overnight. The reaction was concentrated under reduced pressure. The residue was evaporated from twice from toluene, once from hexanes, triturated with hexanes, filtered and dried in vacuo to provide 25 mg (70%) of desired product as the trihydrochloride salt. MS ESI (+) m/z 362 (M+1) detected.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customThe residue was evaporated from twice from toluene
  3. customonce from hexanes, triturated with hexanes
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2900ba3aa5ae4292a26bf23af6c8eab8
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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