Hydrochloric Acid → 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-aminoethyl)benzamide, hydrochloride

HRID 882281Notes

Reaction equation

HRID 882281 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:32]=[CH:31][C:17]([C:18]([NH:20][CH2:21][CH2:22][NH:23]C(=O)OC(C)(C)C)=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][N:35]=2)[CH2:6][C@@H:5]1[CH3:42])(=[O:3])[CH3:2].[ClH:43]>O1CCOCC1>[ClH:43].[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:32]=[CH:31][C:17]([C:18]([NH:20][CH2:21][CH2:22][NH2:23])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][N:35]=2)[CH2:6][C@@H:5]1[CH3:42])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86709419tert-butyl (2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate

Product 1

HCID 714685074-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-aminoethyl)benzamide, hydrochlorideYield 104%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A suspension of tert-butyl (2-(4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate (for a preparation see Intermediate 39)(65 mg, 0.114 mmol) in 1,4-dioxane (1 mL) at room temperature was treated with hydrogen chloride in 1,4-dioxane (4N, 2 mL, 8.00 mmol) and the resulting suspension was stirred at this temperature for 1 h then concentrated in vacuo. The precipitate formed was triturated with Et2O isolated by filtration and dried under vacuum to give 4-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-aminoethyl)benzamide, hydrochloride (60 mg, 0.119 mmol, 104% yield) as a white solid. LCMS (HpH, 2 min), Rt=0.75 min, MH+=469.

Workup

  1. customat room temperature
  2. concentrationthen concentrated in vacuo
  3. customThe precipitate formed
  4. customwas triturated with Et2O
  5. customisolated by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-19ea80fed62a40829159e3ab2c8b51f5
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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