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

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

Participants

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

concentrationAfter concentration in vacuo the residue
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

Linked notes

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