4-Azidooxane → HCID 117777715, compound

HRID 64158Notes

Reaction equation

HRID 64158 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]([CH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)=[N+:31]=[N-:32]>CN(C=O)C.[Cu](I)I>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C:16]1[CH:17]=[C:12]([N:9]2[C:6]3=[N:7][CH:8]=[C:3]([C:1]4[N:32]=[N:31][N:30]([CH:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)[CH:2]=4)[CH:4]=[C:5]3[N:11]=[CH:10]2)[CH:13]=[C:14]([NH:26][C:27](=[O:29])[CH3:28])[CH:15]=1

Participants

5

Reactant 2

HCID 639358444-AzidooxaneHCID 89500199HCID 89500199, compound

Product 1

HCID 117777715HCID 117777715, compoundYield 45%

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 (250 mg, 0.644 mmol), 4-azidotetrahydro-2H-pyran (90 mg, 0.77 mmol, 1.2 eq.), copper iodide (12 mg, 0.06 mmol, 0.1 eq.) in DMF was stirred at 90° C. for 16 h. 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 45% yield (150 mg). 1H NMR (300 MHz, DMSO): δ 10.4 (s, 1H), 8.99-8.97 (m, 2H), 8.88 (s, 1H), 8.61-8.60 (m, 1H), 8.32-8.29 (m, 1H), 7.91 (d, 1H), 7.76-7.68 (m, 2H), 7.48-7.41 (m, 1H), 7.3-7.24 (m, 1H), 4.80 (m, 1H), 4.02 (m, 2H), 3.50-3.60 (m, 2H), 2.10 (s, 3H), 2.0-2.12 (m, 4H); LC-MS (ESI): Calculated mass: 515.5; Observed mass: 516.5 [M+H]+ (rt: 1.37 min).

Workup

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

Sources & evidence

ORD record
ord-8c7ea750746c4ca5aa9c87f0fb182336
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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