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

HRID 2217849Notes

Reaction equation

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

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 688096066-Chloro-N-(cyclohexylmethyl)-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-piperidinyl]-5-quinolinecarboxamide

Product 1

HCID 597686346-Chloro-N-(cyclohexylmethyl)-2-[(3S)-3-[(2-hydroxyethyl)amino]-1-piperidinyl]-5-quinolinecarboxamide

Procedure

Prepared according to the method of example 50(b) using 6-chloro-N-(cyclohexylmethyl)-2-[(3S)-3-[[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]amino]-1-piperidinyl]-5-quinolinecarboxamide Example 52(a)) (190 mg) and hydrochloric acid (4M in 1,4-dioxane) (2.0 mL). Purification (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 96:3:1) and subsequent recrystallisation (acetonitrile) gave the title compound as a solid (53 mg).

Workup

customPrepared
customPurification (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 96:3:1) and subsequent recrystallisation (acetonitrile)

Sources & evidence

ORD record: ord-b49b86deb2834386a2c21510788eb3e3
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

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