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3-Fluoroazetidine → 2-{3-[(3-fluoroazetidin-1-yl)methyl]phenyl}-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

HRID 82093
Notes
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Reaction equation

HRID 82093 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[C:17]([C:19]([C:21]3[C:29]4[CH:28]=[N:27][CH:26]=[N:25][C:24]=4[N:23]([CH:30]([CH3:32])[CH3:31])[CH:22]=3)=[O:20])[CH:18]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)=O.[F:33][CH:34]1[CH2:37][NH:36][CH2:35]1>>[F:33][CH:34]1[CH2:37][N:36]([CH2:1][C:3]2[CH:4]=[C:5]([CH2:9][C:10]([NH:12][C:13]3[CH:14]=[N:15][CH:16]=[C:17]([C:19]([C:21]4[C:29]5[CH:28]=[N:27][CH:26]=[N:25][C:24]=5[N:23]([CH:30]([CH3:32])[CH3:31])[CH:22]=4)=[O:20])[CH:18]=3)=[O:11])[CH:6]=[CH:7][CH:8]=2)[CH2:35]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 36035423-FluoroazetidineHCID 866720722-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

Product 1

HCID 708174872-{3-[(3-fluoroazetidin-1-yl)methyl]phenyl}-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

Procedure

The title compound was prepared according to the method described for Example 266 using 2-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide (Preparation 192, 60 mg, 0.14 mmol) and 3-fluoroazetidine to afford the title compound in 16% yield, 11 mg.

Workup

  • customThe title compound was prepared
  • Sources & evidence

    ORD record
    ord-f48ee245a8074c2cb9304997d80fb423
    Source dataset
    uspto-grants-2014_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08846698B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes