2-([1,2,4]Triazolo[1,5-a]pyridin-2-yl)ethanamine → 2-(2-([1,2,4]Triazolo[1,5-A]pyridin-2-YL)ethyl)-7-chloro-5-methyl-2,3-dihydro-1H-pyrrolo[3,4-C]pyridine-1,6(5H)-dione

HRID 1752602Notes

Reaction equation

[N:1]1[C:2]([CH2:10][CH2:11][NH2:12])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH3:13][N:14]1[CH:19]=[C:18]([CH2:20]Cl)[C:17]([C:22](OC)=[O:23])=[C:16]([Cl:26])[C:15]1=[O:27]>CC#N>[Cl:26][C:16]1[C:15](=[O:27])[N:14]([CH3:13])[CH:19]=[C:18]2[CH2:20][N:12]([CH2:11][CH2:10][C:2]3[N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)[C:22](=[O:23])[C:17]=12

Participants

Conditions

Temperature: 100 °C

Procedure

TEA (3.01 ml, 21.59 mmol) was added rapidly to a solution of 2-([1,2,4]triazolo[1,5-a]pyridin-2-yl)ethanamine (1.167 g, 7.20 mmol) and 1-methyl-2-oxo-1,2-dihydro-3-chloro-4-methoxycarbonyl-5-chloromethyl-pyridine (1.8 g, 7.20 mmol, see compound (6) of Example b1)) in MeCN (15 ml). The reaction was heated in a microwave at about 100° C. for about 40 min. The reaction was cooled to r.t. and the mixture was filtered through a Büchner funnel. The residue solid was triturated with water (2×20 ml). The resulting solid was filtered off on a Büchner funnel to afford the title compound (1.3 g, 3.78 mmol, 52.5% yield).

Workup

temperatureThe reaction was cooled to r.t.
filtrationthe mixture was filtered through a Büchner funnel
customThe residue solid was triturated with water (2×20 ml)
filtrationThe resulting solid was filtered off on a Büchner funnel

Sources & evidence

ORD record: ord-9cd39cf0fd79476792a1c7f58cda7245
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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