HCID 90419107, compound → HCID 90454442, compound

HRID 530830Notes

Reaction equation

COC1C=CC(C[N:8]2[C:13](=[O:14])[C:12]([NH:15][CH2:16][C:17]3[S:18][C:19]([CH3:22])=[N:20][N:21]=3)=[CH:11][C:10]([O:23][CH2:24][C@H:25]3[CH2:27][C@@H:26]3[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][N:29]=3)=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C@H:26]2[CH2:27][C@@H:25]2[CH2:24][O:23][C:10]2[CH:11]=[C:12]([NH:15][CH2:16][C:17]3[S:18][C:19]([CH3:22])=[N:20][N:21]=3)[C:13](=[O:14])[NH:8][N:9]=2)=[N:29][CH:30]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-(4-methoxybenzyl)-6-(((1S,2S)-2-(5-methoxypyridin-2-yl)cyclopropyl)methoxy)-4-(((5-methyl-1,3,4-thiadiazol-2-yl)methyl)amino)pyridazin-3(2H)-one (50 mg, 0.096 mmol) was dissolved in TFA (2 ml) and heated at 60° C. for 24 h. The mixture was cooled and the solvent was evaporated under reduced pressure. The crude was purified by Prep-HPLC to afford title product. LRMS m/z (M+H) 401.1 found, 401.1 required. 1H NMR (400 MHz, MeOD) δ 8.06 (d, 1H), 7.30 (dd, 1H), 7.17 (d, 1H), 5.94 (s, 1H), 4.81 (s, 2H), 4.15 (dd, 1H), 4.04 (dd, 1H), 3.85 (s, 3H), 2.75 (s, 3H), 2.11 (m, 1H), 1.72 (m, 1H), 1.21 (m, 1H), 1.07 (m, 1H).

Workup

temperatureThe mixture was cooled
customthe solvent was evaporated under reduced pressure
customThe crude was purified by Prep-HPLC

Sources & evidence

ORD record: ord-18de88591aa34daa9de3eba5c6f571a0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353104B2

Reaction notes

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