Hydrochloric Acid → HCID 131732648, compound

HRID 882284Notes

Reaction equation

HRID 882284 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][CH:37]=[CH:36][N:35]=2)[CH2:6][C@@H:5]1[CH3:40])(=[O:3])[CH3:2].[ClH:41]>O1CCOCC1>[ClH:41].[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][CH:37]=[CH:36][N:35]=2)[CH2:6][C@@H:5]1[CH3:40])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86709434HCID 86709434, compound

Product 1

HCID 131732648HCID 131732648, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A suspension of tert-butyl (2-(4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)benzamido)ethyl)carbamate (for a preparation see Intermediate 40)(35 mg, 0.064 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 for 1 h at this temperature then concentrated in vacuo. The residue was triturated with Et2O the solid isolated by filtration and dried under house vacuum to give 4-((2S,4R)-1-acetyl-2-methyl-4-(pyridin-2-ylamino)-1,2,3,4-tetrahydroquinolin-6-yl)-N-(2-aminoethyl)benzamide, hydrochloride (30 mg, 0.062 mmol, 97% yield) as a very pale yellow solid. LCMS (HpH, 2 min), Rt=0.74 min, MH+=444.

Workup

  1. customat room temperature
  2. concentrationthen concentrated in vacuo
  3. customThe residue was triturated with Et2O the solid
  4. customisolated by filtration
  5. customdried under house vacuum

Sources & evidence

ORD record
ord-77d735d955d94a06926bd570da316f6c
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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