Pyrrolidine → HCID 90024951, compound

HRID 1055024Notes

Reaction equation

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

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 90017348HCID 90017348, compound

Product 1

HCID 90024951HCID 90024951, compoundYield 41.1%

Procedure

Was prepared in the same manner as described in Example 87a) using (E)-2-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)prop-1-enyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (448 mg, 1.29 mmol, Eq: 1.00) instead of 2-[(E)-2-(5-bromo-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine and pyrrolidine (183 mg, 213 μl, 2.57 mmol, Eq: 2) instead of pyrrolidin-2-one affording 5,8-dimethyl-2-[(E)-2-(2-methyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazol-3-yl)-propenyl]-[1,2,4]triazolo[1,5-a]pyrazine (109 mg, 41.1%) as a white solid. MS: m/z=339.5 (M+H+)

Workup

customWas prepared in the same manner

Sources & evidence

ORD record: ord-46a306e9d3e748928bfc299b0947aa96
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394311B2

Reaction notes

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