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(R)-(-)-1-Aminoindan → HCID 178440432, compound

HRID 383727
Notes
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Reaction equation

HRID 383727 reaction equation
[CH:1]([C:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11](S(C)(=O)=O)[N:10]=2)=[CH:7][NH:6][N:5]=1)([CH3:3])[CH3:2].[C@H:19]1([NH2:28])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1>CS(C)=O.ClCCl>[C@H:19]1([NH:28][C:11]2[N:10]=[C:9]([C:8]3[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][NH:6][CH:7]=3)[CH:14]=[CH:13][N:12]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2733933(R)-(-)-1-AminoindanHCID 178440433HCID 178440433, compound

Product 1

HCID 178440432HCID 178440432, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4-(3-isopropyl-1H-pyrazol-4-yl)-2-methanesulfonyl-pyrimidine (40 mg, 0.15 mmol) in anhydrous DMSO (0.25 mL) is added (R)-indan-1-ylamine (58 uL, 0.45 mmol). The reaction mixture is stirred at 150° C. overnight, diluted with dichloromethane, and washed with water. The organic layer is dried over sodium sulfate and concentrated in vacuo. The crude product is purified by preparative HPLC to provide 20 mg of (R)-indan-1-yl-[4-(3-isopropyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amine. (Example 83).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-015d6843ca684552b18b5f4c3c2d0eea
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367687B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes