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Diisopropylamine → HCID 86651827, compound

HRID 1916131
Notes
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Reaction equation

HRID 1916131 reaction equation
[Br:1][C:2]1[C:3]([NH:9][C@H:10]2[CH2:15][CH2:14][CH2:13]N[CH2:11]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:16](NC(C)C)(C)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[Br:1][C:2]1[C:3]([NH:9][C@H:10]2[CH2:11][CH2:16][CH2:13][CH:14]([S:24]([CH3:23])(=[O:26])=[O:25])[CH2:15]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 31297Methanesulfonyl chlorideHCID 86651828(5-bromo-2-chloro-pyrimidin-4-yl)-(S)-piperidin-3-yl-amine

Product 1

HCID 86651827HCID 86651827, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of (5-bromo-2-chloro-pyrimidin-4-yl)-(S)-piperidin-3-yl-amine (3.5 g, 12.2 mmol) and diisopropylamine (6 g, 46 mmol) in dichloromethane was cooled to 5° C. and treated with methansulfonyl chloride (2.1 g, 18 mmole). After stirring at 20° C. for 2 hours, the reaction was concentrated purified by silica gel chromatography to give 3.1 g (43% from step 1) of (5-Bromo-2-chloro-pyrimidin-4-yl)-((S)-3-methanesulfonyl-cyclohexyl)-amine.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d352f5c09ad34e8a863e50bf5c600b70
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618103B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes