Trifluoroacetic acid → HCID 66851513, compound

HRID 1909474Notes

Reaction equation

O1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[CH:20]=[C:19]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][N:16]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1.[NH2:27][C@H:28]([CH3:31])[CH2:29][OH:30].FC(F)(F)C(O)=O>C(O)CCC>[OH:30][CH2:29][C@H:28]([N:27]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[CH:20]=[C:19]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][N:16]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1)[CH3:31]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of N-(3-(1,3,4-oxadiazol-2-yl)phenyl)-3,4′-bipyridine-2′-carboxamide (210 mg, 0.61 mmol), (R)-2-amino-1-propanol (0.3 mL), and trifluoroacetic acid (0.05 mL) in n-butanol was heated in a microwave to 150° C. for 1 hour. The solvent was removed under reduced pressure and the residue was purified by reverse-phase HPLC to give (R)-N-(3-(4-(1-hydroxypropan-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-3,4′-bipyridine-2′-carboxamide as a white powder (55 mg, 0.138 mmol, 23% yield).

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by reverse-phase HPLC

Sources & evidence

ORD record: ord-18c0fe60d98f4f86a53ebb8bad05a797
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598360B2

Reaction notes

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