Azetidine → HCID 16222609, compound

HRID 1808936Notes

Reaction equation

HRID 1808936 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.[NH:21]1[CH2:24][CH:23]([N:25]2[CH2:29][CH2:28][CH:27]([N:30]([CH3:32])C)[CH2:26]2)[CH2:22]1.N1C[CH2:35][CH2:34]1.O=[C:38]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:21]2[CH2:22][CH:23]([N:25]([CH3:38])[CH2:29][CH2:28][C:27]3[CH:26]=[CH:35][CH:34]=[CH:32][N:30]=3)[CH2:24]2)=[O:7])[CH:8]=[CH:9][C:10]=1[F:11]

Participants

5

Reactant 4

HCID 10422AzetidineHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 220256632-(2-Fluoro-4-iodoanilino)-3,4-difluorobenzoic acidHCID 63164274HCID 63164274, compound

Product 1

HCID 16222609HCID 16222609, compound

Procedure

The title compound was prepared by reacting 3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzoic acid with 1-(azetidin-3-yl)-N,N-dimethylpyrrolidin-3-amine. The azetidine intermediate was preparedusing 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, CD3OD): 8.50 (d, 1H), 7.94 (t, 1H), 7.50-7.30 (m, 5H), 7.07 (q, 1H), 6.66-6.61 (m, 1H), 4.52-4.48 (m, 2H), 4.31 (s, 2H), 4.23-4.18 (m, 1H), 3.48-3.46 (m, 2H), 3.17-3.13 (m, 2H), 2.88 (s, 3H); MS (EI) for C24H22F3IN4O: 567 (MH+).

Workup

  1. customThe title compound was prepared
  2. customwas prepared

Sources & evidence

ORD record
ord-16a5299ab25e462da4603dfd861ec583
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

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