Azetidine → 1-(Azetidin-1-yl)-2-(2,6-difluoro-4-hydroxyphenyl)ethanone

HRID 1474739Notes

Reaction equation

HRID 1474739 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][C:11]([OH:13])=O.[NH:14]1[CH2:17][CH2:16][CH2:15]1.C(N(CC)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:14]1([C:11](=[O:13])[CH2:10][C:3]2[C:4]([F:9])=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[F:1])[CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 847706302,6-Difluoro-4-hydroxyphenylacetic acid

Product 1

HCID 895828981-(Azetidin-1-yl)-2-(2,6-difluoro-4-hydroxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2,6-difluoro-4-hydroxyphenyl)acetic acid (0.98 g, 4.95 mmol) in 8 ml anhydrous DMF at RT was added azetidine (0.565 g, 9.89 mmol) and N,N-diisopropylethylamine (2.15 ml, 12.3 mmol). o-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.76 g, 9.89 mmol) was added to the solution and the reaction mixture was stirred at RT for 4 hrs. The solution was purified by preparative biotage Reverse phase (C-18) (50 g column), eluting with Acetonitrile/Water+0.1% formic acid (35% to 100%), to afford the title compound. LC/MS (m/z) 242.3 (M+15)+.

Workup

  1. customThe solution was purified by preparative biotage Reverse phase (C-18) (50 g column)
  2. washeluting with Acetonitrile/Water+0.1% formic acid (35% to 100%)

Sources & evidence

ORD record
ord-f6f5c7d702be485993914ce2c69b146e
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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