Potassium Iodide → HCID 9978666, compound

HRID 31468

Reaction equation

HRID 31468 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19]([CH3:20])=[C:18]([F:21])[CH:17]=[C:16]([C:22]([NH:24][CH:25]4[CH2:27][CH2:26]4)=[O:23])[CH:15]=3)=[CH:10][CH:9]=2)=[N:5][N:4]=1.[I-].[K+]>C1(N)CC1>[CH:25]1([NH:24][C:22]([C:16]2[CH:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:6]4[O:7][C:3]([CH2:2][NH:24][CH:25]5[CH2:27][CH2:26]5)=[N:4][N:5]=4)=[CH:9][CH:10]=3)[C:19]([CH3:20])=[C:18]([F:21])[CH:17]=2)=[O:23])[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 693149174'-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1'-biphenyl-3-carboxamide2×

Product 1

HCID 9978666HCID 9978666, compound

Reagents, catalysts & solvents 1

HCID 69828CyclopropylamineSolvent

Procedure

4′-[5-(Chloromethyl)-1,3,4-oxadiazol-2-yl]-N-cyclopropyl-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide (Intermediate 34) (50 mg) and potassium iodide (22 mg) were stirred in cyclopropylamine (2 ml) for 48 hours. The reaction was absorbed onto silica and purified by chromatography on a biotage column (silica, 9 g), eluting with DCM/methanol (99:1). The product fractions were reduced to dryness under vacuum to give N-cyclopropyl-4′-{5-[(cyclopropylamino)methyl]-1,3,4-oxadiazol-2-yl}-5-fluoro-6-methyl-1,1′-biphenyl-3-carboxamide.

Workup

  1. customThe reaction was absorbed onto silica
  2. custompurified by chromatography on a biotage column (silica, 9 g)
  3. washeluting with DCM/methanol (99:1)

Sources & evidence

ORD record
ord-4cbeb6e1246742cdbcdba57395bf4873
Source dataset
uspto-grants-2008_09
Patent number
US07425555B2

Linked notes

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