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Sodium hydride → (S)-N-(1-{4-[3-(2-Cyclopropylmethoxy-pyridin-4-yloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

HRID 40526
Notes
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Reaction equation

HRID 40526 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:12][N:11]([C:13]3[CH:18]=[CH:17][C:16]([C@@H:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])=[CH:15][CH:14]=3)[CH2:10]2)[CH:5]=[CH:4][N:3]=1.[CH:25]1([CH2:28][OH:29])[CH2:27][CH2:26]1.[H-].[Na+]>O1CCOCC1>[CH:25]1([CH2:28][O:29][C:2]2[CH:7]=[C:6]([O:8][CH:9]3[CH2:12][N:11]([C:13]4[CH:18]=[CH:17][C:16]([C@@H:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])=[CH:15][CH:14]=4)[CH2:10]3)[CH:5]=[CH:4][N:3]=2)[CH2:27][CH2:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 86689013(S)-N-(1-{4-[3-(2-Fluoro-pyridin-4-yloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

Product 1

HCID 86689027(S)-N-(1-{4-[3-(2-Cyclopropylmethoxy-pyridin-4-yloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-Dioxane
Solvent

Conditions

Temperature
130 °C

Procedure

To 55 mg (0.17 mmol) (S)—N-(1-{4-[3-(2-Fluoro-pyridin-4-yloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide (XI.1) in 5 mL 1,4-dioxane is added 0.14 mL (1.73 mmol) cyclopropanemethanol. 38 mg (0.95 mmol, 60% suspension in mineral oil) NaH is added and the mixture is stirred for 15 h at 130° C. After concentration in vacuo the residue is purified by chormotography (silica, ethylacetate) to yield the desired product.

Workup

  1. concentrationAfter concentration in vacuo the residue
  2. customis purified by chormotography (silica, ethylacetate)

Sources & evidence

ORD record
ord-a056d0b03c8f4f7e94bd433ec3b60523
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530461B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes