Water → HCID 49806124, compound

HRID 1615070Notes

Reaction equation

[CH:1]1([C:4]2[CH:36]=[CH:35][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:19][N:18]([C:20]([C:22]5[CH:27]=[C:26]([O:28][CH2:29][C@H:30]6C[O:31]6)[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:17]4)=[CH:12][C:11]=3[O:33][CH3:34])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.O.[CH3:38][N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1.[C:45](#N)C>>[CH:1]1([C:4]2[CH:36]=[CH:35][C:7]([CH2:8][O:9][C:10]3[CH:15]=[CH:14][C:13]([CH:16]4[CH2:17][N:18]([C:20]([C:22]5[CH:27]=[C:26]([O:28][CH2:29][C@H:30]([OH:31])[CH2:38][N:39]6[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]6)[CH:25]=[CH:24][N:23]=5)=[O:21])[CH2:19]4)=[CH:12][C:11]=3[O:33][CH3:34])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

Reactant 4

HCID 962Water

HCID 6342Acetonitrile

HCID 531671-Methylpiperazine

HCID 59633909HCID 59633909, compound2×

Product 1

HCID 49806124HCID 49806124, compoundYield 80%

Procedure

To a mixed solution of {3-[4-(4-cyclopropylbenzyloxy)-3-methoxyphenyl]azetidin-1-yl}-[4-((R)-1-oxiranylmethoxy)-pyridin-2-yl]-methanone (0.45 g) prepared in (1) in acetonitrile (4.0 mL)/water (1.0 mL) was added 1-methylpiperazine (1.0 mL). The reaction mixture was stirred at RT for 12 hr. The reaction mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=9/1) to give the title compound (0.43 g, 80%).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe residue was purified by silica gel chromatography (Developing solvent: chloroform/methanol=9/1)

Sources & evidence

ORD record: ord-475843c018964d56a9c4f92f2775eef3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765739B2

Reaction notes

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