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Hydrochloric Acid → 6-Chloro-N-[(1-hydroxycycloheptyl)methyl]-2-{(3S)-3-[(2-hydroxyethyl)amino]-pyrrolidin-1-yl}quinoline-5-carboxamide

HRID 424767
Notes
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Reaction equation

HRID 424767 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:23]([C:27]([NH:29][CH2:30][C:31]4([OH:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:28])=[C:22]([Cl:39])[CH:21]=[CH:20][C:19]=3[N:18]=2)[CH2:13]1)(C(C)(C)C)(C)C.Cl>O1CCCC1>[Cl:39][C:22]1[CH:21]=[CH:20][C:19]2[N:18]=[C:17]([N:14]3[CH2:15][CH2:16][C@H:12]([NH:11][CH2:10][CH2:9][OH:8])[CH2:13]3)[CH:26]=[CH:25][C:24]=2[C:23]=1[C:27]([NH:29][CH2:30][C:31]1([OH:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 577339922-{(3S)-3-[(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)amino]pyrrolidin-1-yl}-6-chloro-N-[(1-hydroxycycloheptyl)methyl]quinoline-5-carboxamide

Product 1

HCID 577339916-Chloro-N-[(1-hydroxycycloheptyl)methyl]-2-{(3S)-3-[(2-hydroxyethyl)amino]-pyrrolidin-1-yl}quinoline-5-carboxamideYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Procedure

To a solution of 2-{(3S)-3-[(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)amino]pyrrolidin-1-yl}-6-chloro-N-[(1-hydroxycycloheptyl)methyl]quinoline-5-carboxamide (26.0 g) in tetrahydrofuran (125 ml) was added hydrogen chloride (50 ml, 4M in dioxane) dropwise over ten minutes with ice bath cooling to maintain the internal temperature below 30° C. The mixture was stirred at room temperature for 2.5 hours before being concentrated in vacuo. The crude product was redissolved in MeOH (30 ml) and purified by chromatography (SiO2, 1:4:95-1:10:89 7M N3 in methanol:methanol:dichloromethane as gradient elution). The pure fractions were concentrated in vacuo (20.1 g) and then slurried in acetonitrile:methanol (99:1, 400 ml total volume) for 18 hours before being filtered and washed with acetonitrile (30 ml). The solid was dried in vacuo to afford the title compound as a colourless solid (18.5 g).

Workup

  1. temperaturecooling
  2. temperatureto maintain the internal temperature below 30° C
  3. concentrationbefore being concentrated in vacuo
  4. dissolutionThe crude product was redissolved in MeOH (30 ml)
  5. custompurified by chromatography (SiO2, 1:4:95-1:10:89 7M N3 in methanol:methanol:dichloromethane as gradient elution)
  6. concentrationThe pure fractions were concentrated in vacuo (20.1 g)
  7. waitslurried in acetonitrile:methanol (99:1, 400 ml total volume) for 18 hours
  8. filtrationbefore being filtered
  9. washwashed with acetonitrile (30 ml)
  10. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-fe47982b68ff4ec691fb8cdbe4a2a754
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106073B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes