Hydrochloric Acid → N-[6-Chloro-2-[(3S)-3-[(2-hydroxyethyl)amino]-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide

HRID 2217858Notes

Reaction equation

HRID 2217858 reaction equation
[Cl:1][C:2]1[C:3]([NH:29][C:30](=[O:38])[CH2:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH2:13]1)[CH:6]=[CH:5]2.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([NH:29][C:30](=[O:38])[CH2:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH2:15][C@H:14]([NH:18][CH2:19][CH2:20][OH:21])[CH2:13]1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68808571N-[6-Chloro-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 11385256N-[6-Chloro-2-[(3S)-3-[(2-hydroxyethyl)amino]-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamideYield 35.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Prepared according to the method of example 50(b), using N-[6-chloro-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-piperidinyl]-5-quinolinyl]-cyclohexaneacetamide (Example 61(a)) (200 mg) and 4M hydrogen chloride in 1,4-dioxane (2 mL). Purification (SiO2, methanol:dichloromethane 5:95 as eluant) gave the title compound as a solid (56 mg).

Workup

  1. customPrepared
  2. customPurification (SiO2, methanol:dichloromethane 5:95 as eluant)

Sources & evidence

ORD record
ord-095545e3ad7247be986242ec03a56088
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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