Water → HCID 178519485, compound

HRID 2104518Notes

Reaction equation

HRID 2104518 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([CH:33]=[CH:34][CH:35]=1)[O:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]#[N:32])=[CH:26][CH:25]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:36]([F:39])([F:38])[F:37])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:40]=[N+:41]=[N-:42].[Na+].[NH4+].[Cl-].O>CN(C=O)C>[C:2]1([C:1]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:35]=[CH:34][CH:33]=[C:21]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][C:27]([CH2:30][C:31]5[NH:42][N:41]=[N:40][N:32]=5)=[CH:26][CH:25]=4)[CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:36]([F:38])([F:37])[F:39])=[O:8])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 66913235HCID 66913235, compound

Product 1

HCID 178519485HCID 178519485, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ([4-({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}methyl) phenyl]acetonitrile) (0.52 g, 1.0 mmol), sodium azide (0.33 g, 5.0 mmol) and NH4Cl (0.27 g, 5 mmol) in DMF (30 ml) was heated to 125° C. After 48 hr, the reaction was cooled and poured into water. The aqueous layer was extracted with EtOAc, dried and concentrated. The product was purified by column chromatography (eluent 50% EtOAc/Hexane) to give the title compound as a foam (0.12 g, 22%); MS (ESI) m/z [M+H]+(566); 1H NMR (DMSO) δ 16.2 (s, 1H), 9.13 (s, 1H), 8.32 (d, 1H, J=6.7 Hz), 7.92 (d, 1H, J=8.4 Hz), 7.75 (t, 1H, J=7.8 Hz), 7.63 (d, 2H, J=8.4 Hz), 7.57-7.53 (m, 1H), 7.39-7.25 (m, 7H), 6.98-6.93 (m, 2H), 6.84 (d, 1H, J=8.2 Hz), 5.02-4.43 (m, 2H), 4.32 (s, 2H).

Workup

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography (eluent 50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-7aa67177eb2149099b0b96cfddc4bb89
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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