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1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(7-Chloro-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 404742
Notes
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Reaction equation

HRID 404742 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([SH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[CH:22]=[N:21][CH:20]=[CH:19]2.C1CCN2C(=NCCC2)CC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][C:25]=2[Cl:26])[CH:22]=[N:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylateHCID 534186156-Bromo-7-chloroisoquinoline

Product 1

HCID 592908234-(7-Chloro-isoquinolin-6-ylsulfanyl)-piperidine-1-carboxylic acid tert-butyl esterYield 73.6%

Conditions

Temperature
80 °C

Procedure

To 1.78 g of crude 4-Mercapto-piperidine-1-carboxylic acid tert-butyl ester (273) were dissolved in 20 ml degassed DMF was added 1.3 g (7.1 mmol) 6-Fluoro-7-chloroisoquinoline (263) and 1.23 ml (8.2 mmol) DBU. After stirring for 90 min at 80° C. the solvent was evaporated. The residue was taken up in ethyl acetate and washed with brine. The organic phases were dried over Sodium sulfate and evaporated. Purification over silica gel (40% to 60% ethyl acetate in heptane) gave 1.98 g of the expected compound.

Workup

  1. customdegassed DMF
  2. customwas evaporated
  3. washwashed with brine
  4. dry with materialThe organic phases were dried over Sodium sulfate
  5. customevaporated
  6. customPurification over silica gel (40% to 60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-ac1f9ae16485495e81157a195d46f614
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748614B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes