Hydrochloric Acid → HCID 178480126, compound

HRID 2355129Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[O:12][C:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[CH:22]=[C:21]([O:26][CH2:27][C:28]#[N:29])[CH:20]=[CH:19]4)=[CH:14][N:15]=2)=[CH:3]1.[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[O:12][C:13]([C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[C:21]([O:26][CH2:27][C:28]5[NH:32][N:31]=[N:30][N:29]=5)[CH:22]=4)[CH:17]=3)=[CH:14][N:15]=2)=[CH:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ({6-[2-(1-methyl-1H-indol-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetonitrile (313 mg, 0.826 mmol), prepared in the previous step, sodium azide (163 mg, 2.5 mmol) and ammonium chloride (134 mg, 2.5 mmol) in 20 mL of DMF was stirred under nitrogen at 100° C. for 5 h. Following the reaction by MS, starting material remained. Additional sodium azide (165 mg, 2.6 mmol) and ammonium chloride(134 mg, 2.5 mmol) were added and the reaction stirred at 100° C. for two more hours. This procedure was repeated three additional times until the MS showed that the reaction had gone to completion. The reaction was acidified with 25 mL of 1N HCl and then diluted with 25 mL of H2O. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (287 mg, 82%) as a brown solid, mp 254-256° C. Elemental Analysis for C24H18N6O2+0.71 H2O Calc'd: C, 66.23; H, 4.50; N, 19.31. Found: C, 63.15; H, 4.17; N, 18.00.

Workup

customthe reaction by MS
stirringthe reaction stirred at 100° C. for two more hours
customThe solid that formed
filtrationwas collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-f59850a6bb4d42f2a4987c3ace20f494
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754747B2

Reaction notes

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