HCID 66723670, compound → HCID 56836122, compound

HRID 928359Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH2:15][NH:16][C:17]([C:19]2[N:23]=[C:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:21]([CH3:31])[N:20]=2)=[O:18])=[C:10]([CH3:32])[N:9]=1)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[NH2:7][C:8]1[N:9]=[C:10]([CH3:32])[C:11]([CH2:15][NH:16][C:17]([C:19]2[N:23]=[C:22]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:21]([CH3:31])[N:20]=2)=[O:18])=[C:12]([CH3:14])[CH:13]=1

Participants

Conditions

Temperature: 23 °C

Procedure

(5-{[(5-Benzyl-1-methyl-1H-[1,2,4]triazole-3-carbonyl)-amino]-methyl}-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (29 mg, 0.064 mmol) was dissolved in a mixture of dichloromethane (4 ml) and TFA (1 ml). The reaction mixture was shaken at 23° C. for 18 h. Solvents were removed in vacuo. The residue was dissolved in dichloromethane/methanol 1:1 (1 ml) and purified over VARIAN SCX-SPE cartridge (strong cation exchange), washing with methanol and releasing the compound with 2M ammonia in methanol. The basic fraction was evaporated in vacuo to give the title compound. 1H-NMR (DMSO, 400 MHz) 8.5 (s, 1H), 7.2-7.3 (m, 5H), 7.0 (br s, 2H) 6.5 (s, 1H), 4.3 (d, 2H), 4.2 (s, 2H), 3.8 (s, 3H), 2.4 (s, 3H), 2.3 (s, 3H). UPLC-MS (method F) Rt=0.92 min, [M+H]+=351.4. HPLC (method G) Rt=1.281 min.

Workup

customSolvents were removed in vacuo
dissolutionThe residue was dissolved in dichloromethane/methanol 1:1 (1 ml)
custompurified over VARIAN SCX-SPE cartridge (strong cation exchange)
washwashing with methanol
customThe basic fraction was evaporated in vacuo

Sources & evidence

ORD record: ord-b80a4cae80d34d029e5b2ec89621da9b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290485B2

Reaction notes

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