Hydrochloric Acid → HCID 70976538, compound

HRID 882289Notes

Reaction equation

HRID 882289 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH2:24][NH:25]C(=O)OC(C)(C)C)=[O:21])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[CH2:6][C@@H:5]1[CH3:41])(=[O:3])[CH3:2].Cl>O1CCOCC1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH2:24][NH2:25])=[O:21])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)[CH2:6][C@@H:5]1[CH3:41])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86709436HCID 86709436, compound

Product 1

HCID 70976538HCID 70976538, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1,1-dimethylethyl (2-{[(4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}phenyl)carbonyl]amino}ethyl)carbamate (for a preparation see Intermediate 45) (57 mg, 0.099 mmol) in 1,4-dioxane (0.5 mL) at room temperature was treated with hydrogen chloride in 1,4-dioxane (2 mL, 8.0 mmol) and the resulting mixture was stirred at room temperature for 1.5 h then concentrated in vacuo. The residue was co-evaporated with Et2O to give 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}-N-(2-aminoethyl)benzamide (32.5 mg, 0.063 mmol, 64.1% yield) hydrochloride as a pale yellow solid. LCMS (HpH, 2 min), Rt=1.01 min, MH+=477.

Workup

  1. customat room temperature
  2. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-2d61786186f7470d87da1a36479aefff
Source dataset
uspto-grants-2015_03
Patent number
US08993554B2

Reaction notes

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