3,3-Difluoroazetidine hydrochloride → 6-(3,3-Difluoro-azetidin-1-yl)-N-(3-iodo-4-methyl-phenyl)-nicotinamide

HRID 2190560Notes

Reaction equation

HRID 2190560 reaction equation
Cl[C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([I:16])[CH:10]=2)=[O:7])=[CH:4][N:3]=1.Cl.[F:20][C:21]1([F:25])[CH2:24][NH:23][CH2:22]1.IC1C=C(NC(=O)C2C=CC(N3CCOCC3)=NC=2)C=CC=1C>>[F:20][C:21]1([F:25])[CH2:24][N:23]([C:2]2[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([I:16])[CH:10]=3)=[O:7])=[CH:4][N:3]=2)[CH2:22]1

Participants

4

Reactant 3

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 79255626-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamideHCID 17541675N-(3-Iodo-4-methyl-phenyl)-6-morpholin-4-yl-nicotinamide

Product 1

HCID 593181306-(3,3-Difluoro-azetidin-1-yl)-N-(3-iodo-4-methyl-phenyl)-nicotinamideYield 40%

Procedure

6-(3,3-Difluoro-azetidin-1-yl)-N-(3-iodo-4-methyl-phenyl)-nicotinamide was prepared from 6-chloro-N-(3-iodo-4-methyl-phenyl)-nicotinamide and 3,3-difluoroazetidine hydrochloride in a manner similar to the one described in the synthesis of N-(3-Iodo-4-methyl-phenyl)-6-morpholin-4-yl-nicotinamide above. The product was isolated after silica gel column purification with 20-30% EtOAc in hexanes to afford the product (23 mg. Yield: 40%). HRMS m/z calcd for C16H14N3OFI [M+H]+: 430.0223. Found: 430.0224.

Workup

  1. customThe product was isolated
  2. customafter silica gel column purification with 20-30% EtOAc in hexanes
  3. customto afford the product (23 mg. Yield: 40%)

Sources & evidence

ORD record
ord-a9b1db90ddcd465ab04c601fed358529
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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