Hydrochloric Acid → HCID 17838229, compound

HRID 1352127Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=O)[CH2:12][NH:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:14]([NH:13][CH2:12][CH2:11][NH:10][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]2)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

N1-(1H-5-Indazolyl)-2-(benzylamino)acetamide (Example 173) (56 mg) was dissolved in tetrahydrofuran (1 ml), and a borane-tetrahydrofuran complex (1.0 ml) was added to the solution at room temperature. The reaction mixture was stirred at 50° C. for 6 hr, and 1 N hydrochloric acid (0.5 ml) was then added, followed by stirring at the same temperature for one hr. A saturated aqueous sodium hydrogencarbonate solution (2 ml) was added thereto, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by preparative TLC [chloroform/methanol] to give the title compound (23 mg, yield 43%)

Workup

additiona borane-tetrahydrofuran complex (1.0 ml) was added to the solution at room temperature
stirringby stirring at the same temperature for one hr
extractionthe mixture was extracted with chloroform-propanol (3/1)
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customthe solvent was removed by distillation under the reduced pressure
customThe residue was purified by preparative TLC [chloroform/methanol]

Sources & evidence

ORD record: ord-b80fbeaa03f34f0a9090fe1df3e936bb
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217722B2

Reaction notes

Loading…