Pyrrolidine → HCID 123856582, compound

HRID 1054952Notes

Reaction equation

Br[C:2]1[N:6]=[C:5]([CH:7]=[CH:8][C:9]2[N:19]=[C:12]3[C:13]([CH3:18])=[N:14][CH:15]=[C:16]([CH3:17])[N:11]3[N:10]=2)[N:4]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:3]=1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:4]2[C:5]([CH:7]=[CH:8][C:9]3[N:19]=[C:12]4[C:13]([CH3:18])=[N:14][CH:15]=[C:16]([CH3:17])[N:11]4[N:10]=3)=[N:6][C:2]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[N:3]2)=[CH:22][CH:23]=1

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 123785140HCID 123785140, compound

Product 1

HCID 123856582HCID 123856582, compoundYield 42.8%

Procedure

Was prepared in the same manner as described in General Procedure Example 9 using 2-(2-(3-bromo-1-(4-methoxybenzyl)-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (55 mg, 125 μmol, Eq: 1.00) and pyrrolidine (17.8 mg, 20.7 μl, 250 μmol, Eq: 2) as starting materials. Chromatography afforded 2-{2-[2-(4-Methoxy-benzyl)-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl]-vinyl}-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (23 mg, 42.8%) as a light yellow solid. MS: m/z=431.5 (M+H+)

Workup

customWas prepared in the same manner

Sources & evidence

ORD record: ord-7fad47447966444ebd7ab89ed03dd28b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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