Sodium Azide → HCID 178474041, compound

HRID 64160Notes

Reaction equation

HRID 64160 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[N:11]=[CH:10][N:9]([C:12]3[CH:13]=[C:14]([NH:26][C:27](=[O:29])[CH3:28])[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=4[F:25])[CH:17]=3)[C:6]2=[N:7][CH:8]=1)#[CH:2].[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C=O)C.[Cu](I)I>[NH:30]1[CH:2]=[C:1]([C:3]2[CH:4]=[C:5]3[N:11]=[CH:10][N:9]([C:12]4[CH:13]=[C:14]([NH:26][C:27](=[O:29])[CH3:28])[CH:15]=[C:16]([C:18]5[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=5[F:25])[CH:17]=4)[C:6]3=[N:7][CH:8]=2)[N:32]=[N:31]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 89500199HCID 89500199, compound

Product 1

HCID 178474041HCID 178474041, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture N-(5-(6-ethynyl-3H-imidazo[4,5-b]pyridin-3-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (300 mg, 0.77 mmol), sodium azide (75 mg, 1.15 mmol, 1.5 eq.), copper iodide (14 mg, 0.07 mmol, 0.1 eq.) in DMF was stirred for 16 h at RT. The mixture was quenched with water and the precipitate formed was filtered and dried to give the crude product which was purified by preparative HPLC to give the product in 90% yield (300 mg).

Workup

  1. customThe mixture was quenched with water
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. customdried

Sources & evidence

ORD record
ord-acc47a8af9444ab691e07dbcb77dd3a5
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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