3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → 1-[1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}-carbonyl)azetidin-3-yl]-N,N-dimethylpyrrolidin-3-amine

HRID 605679Notes

Reaction equation

HRID 605679 reaction equation
[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:14]=2[F:20])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.C[N:22]([CH2:27][CH2:28][C:29]1[CH:34]=CC=[CH:31][N:30]=1)[CH:23]1[CH2:26][NH:25][CH2:24]1.O=[C:36]1CN(C(OC(C)(C)C)=O)C1>>[F:1][C:2]1[C:3]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:14]=2[F:20])=[C:4]([C:5]([N:25]2[CH2:24][CH:23]([N:22]3[CH2:27][CH2:28][CH:29]([N:30]([CH3:31])[CH3:36])[CH2:34]3)[CH2:26]2)=[O:7])[CH:8]=[CH:9][C:10]=1[F:11]

Participants

4

Reactant 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 220256632-(2-Fluoro-4-iodoanilino)-3,4-difluorobenzoic acidHCID 62785927N-Methyl-N-[2-(pyridin-2-yl)ethyl]azetidin-3-amine

Product 1

HCID 162226061-[1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}-carbonyl)azetidin-3-yl]-N,N-dimethylpyrrolidin-3-amine

Procedure

The title compound was prepared by reacting 3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoic acid with N-methyl-N-(2-(pyridin-2-yl)ethyl)azetidin-3-amine. The azetidine intermediate was prepared using procedures similar to those described in Abdel-Magid, et. al., Tetrahedron Letters 1990, 31(39), 5595 starting with tert-butyl 3-oxoazetidine-1-carboxylate, which itself was prepared as described in Example 3. The title compound: 1H NMR (400 MHz, d6-DMSO): 8.56 (s, 1H), 7.58 (m, 1H), 7.38 (d, 1H), 7.31 (m, 1H), 7.16 (m, 1H), 6.67 (m, 1H), 4.16 (m, 1H), 3.97 (m, 2H), 3.77 (m, 1H), 3.26 (br s, 4H), 2.63 (m, 1H), 2.42 (br s, 6H), 1.99 (br s, 1H), 1.74 (br s, 1H). MS (EI) for C22H24F3IN4O: 545 (MH+).

Workup

  1. customThe title compound was prepared
  2. customThe azetidine intermediate was prepared
  3. customwas prepared

Sources & evidence

ORD record
ord-242dc743f5a544298ffc6f6d3270ebe3
Source dataset
uspto-grants-2011_03
Patent number
US07915250B2

Reaction notes

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