Hydrochloric Acid → HCID 178420209, compound

HRID 2355133Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of [6-(2-benzyl-oxazol-5-yl)-naphthalen-2-yloxy]-acetonitrile (618 mg, 1.82 mmol), prepared in the previous step, sodium azide (355 mg, 5.46 mmol) and ammonium chloride (312 mg, 5.83 mmol) in 50 mL of DMF was stirred under nitrogen at 100° C. for 5 h. Following the reaction by MS, starting material remained. Additional sodium azide (351 mg, 5.44 mmol) and ammonium chloride (316 mg, 5.85 mmol) were added and the reaction stirred at 100° C. for two more hours. The reaction was at first diluted with 10 ml of H2O, then was made basic with 1N NaOH and finally acidified with 1N HCl. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (568 mg, 82%) as a white solid, mp 227-228° C. Elemental Analysis for C22H17N5O2+0.37 H2O Calc'd: C, 67.74; H, 4.58; N, 17.95. Found: C, 67.84; H, 4.33; N, 18.09

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-5373d9ec37944bb19a3643492c1ebaf2
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754747B2

Reaction notes

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