Potassium Carbonate → HCID 90025225, compound

HRID 1055021Notes

Reaction equation

Br[CH2:2][CH2:3][O:4][CH3:5].[Cl:6][C:7]1[CH:8]=[C:9]([OH:30])[C:10]2[N:11]([N:14]=[C:15]([CH2:17][CH2:18][C:19]3[N:23]([CH3:24])[N:22]=[C:21]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:20]=3)[N:16]=2)[C:12]=1[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Cl:6][C:7]1[CH:8]=[C:9]([O:30][CH2:2][CH2:3][O:4][CH3:5])[C:10]2[N:11]([N:14]=[C:15]([CH2:17][CH2:18][C:19]3[N:23]([CH3:24])[N:22]=[C:21]([N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)[N:20]=3)[N:16]=2)[C:12]=1[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

1-Bromo-2-methoxyethane (10.7 mg, 7.26 μl, 77.3 μmol, Eq: 1.2) was added to 6-chloro-5-methyl-2-(2-(1-methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)ethyl)-[1,2,4]triazolo[1,5-a]pyridin-8-ol (23.3 mg, 64.4 μmol, Eq: 1.00) and K2CO3 (26.7 mg, 193 μmol, Eq: 3) in dimethylformamide (1 ml). The mixture was stirred at 50° C. for 2 h. The crude material was purified by preparative HPLC to give the desired product (7 mg, 25%) as a white powder. MS: m/z=420.6 (M+H+)

Workup

customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record: ord-594651337c1d4d1e82e97c92b2dd0370
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

Loading…