Hydrochloric Acid → HCID 178420306, compound

HRID 2355122Notes

Reaction equation

HRID 2355122 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[CH:28]=[C:27]([O:32][CH2:33][C:34]#[N:35])[CH:26]=[CH:25]4)=[CH:20][N:21]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:36]=[N+:37]=[N-:38].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[O:18][C:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:32][CH2:33][C:34]5[NH:38][N:37]=[N:36][N:35]=5)[CH:28]=4)[CH:23]=3)=[CH:20][N:21]=2)=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 68452787HCID 68452787, compound

Product 1

HCID 178420306HCID 178420306, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ({6-[2-(1-benzyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetonitrile (104 mg, 0.228 mmol), prepared in the previous step, sodium azide (46.4 mg, 0.715 mmol) and ammonium chloride (36.9 mg, 0.69 mmol) in 10 mL of DMF was stirred at 100° C. for 5 h. Following the reaction by MS, starting material remained. Additional sodium azide (48.9 mg, 0.724 mmol) and ammonium chloride (37.6 mg, 0.71 mmol) were added and the reaction stirred at 100° C. for 2 h. This procedure was repeated until the MS showed that the reaction had gone to completion (three additional times). The reaction was acidified with 10 mL of 1N HCl and then diluted with 10 mL of H2O. The solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (102 mg, 90%) as a tan solid, mp 244-246° C. Elemental Analysis for C30H22N6O2+0.31 H2O Calc'd: C, 71.48; H, 4.52; N, 16.67. Found: C, 69.55; H, 4.55; N, 16.15.

Workup

  1. customthe reaction by MS
  2. stirringthe reaction stirred at 100° C. for 2 h
  3. customThe solid that formed
  4. filtrationwas collected by filtration
  5. washrinsed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5c05f2053f9545069a6047382b9c2165
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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