Isopropanol → HCID 178483035, compound

HRID 1159686Notes

Reaction equation

HRID 1159686 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]#[N:10])=[C:6]([N:11]([CH3:13])[CH3:12])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=3)=[O:23])=[CH:17][CH:16]=2)[N:3]=1.[N-:34]=[N+:35]=[N-:36].[Na+].CC(O)C>[Br-].[Br-].[Zn+2].O.CCOC(C)=O.O1CCOCC1>[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[NH:36][N:35]=[N:34][N:10]=2)=[C:6]([N:11]([CH3:13])[CH3:12])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=3)=[O:23])=[CH:17][CH:16]=2)[N:3]=1

Participants

8

Reactant 3

HCID 3776IsopropanolHCID 33557Sodium AzideHCID 46908652HCID 46908652, compound

Product 1

HCID 178483035HCID 178483035, compoundYield 31.2%

Reagents, catalysts & solvents 4

HCID 10421208Zinc bromideCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution containing N-(4-{[4-chloro-5-(cyanomethyl)-6-(dimethylamino)pyrimidin-2-yl]methyl}phenyl)-2-naphthamide (0.279 g, 0.61 mmol), sodium azide (0.159 g, 2.44 mmol), zinc dibromide (0.345 g, 1.55 mmol), 2-propanol (2.7 mL), water (4 mL), and 1,4-dioxane (5 mL) was heated at reflux for 24 hours. After cooling to room temperature, EtOAc (4 mL) was added and stirring was continued for 2 hours. The resulting mixture was poured into water and the precipitate thus formed was collected by suction, rinsed with water and MeOH, and dried in vacuo to give N-(4-{[4-chloro-6-(dimethylamino)-5-(1H-tetrazol-5-ylmethyl)pyrimidin-2-yl]methyl}-phenyl)-2-naphthamide as a light beige solid (0.095 g, 31%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customthe precipitate thus formed
  4. customwas collected by suction
  5. washrinsed with water and MeOH
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9454981ff2834891adcfd37c15592d15
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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