Pyridine → tert-butyl 2-(3-(6-(5-(N-tert-butylsulfamoyl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)ureido)ethylcarbamate

HRID 384745Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([N:21]=[C:22]([NH2:24])[N:23]=3)[CH:20]=2)[CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:32](Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl.[C:43]([NH:50][CH2:51][CH2:52][NH2:53])([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44]>O1CCCC1>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([N:21]=[C:22]([NH:24][C:32](=[O:34])[NH:53][CH2:52][CH2:51][NH:50][C:43](=[O:44])[O:45][C:46]([CH3:47])([CH3:48])[CH3:49])[N:23]=3)[CH:20]=2)[CH:12]=[N:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 35 °C

Procedure

5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-pyridine-3-sulfonic acid tert-butylamide (50 mg, 0.14 mmol) was suspended in tetrahydrofuran:pyridine (30 mL, 5:1) and cooled to 0° C. Triphosgene (41 mg, 0.14 mmol) was added in one portion and the reaction mixture heated at 35° C. for 2 hours. After this time the solvent was decanted and the resultant semi-solid dissolved in DMF:pyridine (1 mL, 10:1), N-Boc-ethylenediamine (50 mg, 0.32 mmol) was added in one portion and the reaction mixture heated for 18 hours at 65° C. The desired product was isolated as a white solid, directly from the reaction mixture, by preparative HPLC (35 mg)

Workup

customAfter this time the solvent was decanted
dissolutionthe resultant semi-solid dissolved in DMF
temperaturethe reaction mixture heated for 18 hours at 65° C

Sources & evidence

ORD record: ord-5aa9dafbd91f4732a1ef4dfc1d492170
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367830B2

Reaction notes

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