Azetidine → 1-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-chlorophenyl]ethanone

HRID 1850721Notes

Reaction equation

HRID 1850721 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[C:11]([Cl:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:20]1[CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:20]1([C:16](=[O:18])[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[Cl:19])[CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 42417462-(4-(Benzyloxy)-2-chlorophenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 867111801-(Azetidin-1-yl)-2-[4-(benzyloxy)-2-chlorophenyl]ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[4-(benzyloxy)-2-chlorophenyl]acetic acid (0.52 g, 1.88 mmol) was dissolved in DMF (1 ml) and azetidine (0.161 g, 2.82 mmol), DIEA (0.99 ml, 5.64 mmol), and HATU (1.43 g, 3.76 mmol) added. The mixture was stirred at RT for 1 hr. The solution was loaded directly onto a Biotage RP C18 cartridge (30 g) and purified using a gradient eluant of 10-100% water:acetonitrile+0.05% formic acid. The volatiles were removed in vacuo to afford the title compound. LC/MS (m/z): 316 (M+H)+.

Workup

  1. custompurified
  2. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-f5f0927103574778844c85190b826c01
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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