1-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone → HCID 58190549, compound

HRID 1892343Notes

Reaction equation

HRID 1892343 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([C:22](=O)[CH3:23])[N:20]=2)[N:15]=[N:14]1.Cl.[NH:26]1[CH2:30][CH2:29][C@H:28]([O:31][NH2:32])[CH2:27]1>>[NH:26]1[CH2:30][CH2:29][C@H:28]([O:31]/[N:32]=[C:22](/[C:19]2[N:20]=[C:21]3[N:13]([CH2:12][C:3]4[CH:4]=[C:5]5[C:10](=[CH:11][C:2]=4[F:1])[N:9]=[CH:8][CH:7]=[CH:6]5)[N:14]=[N:15][C:16]3=[N:17][CH:18]=2)\[CH3:23])[CH2:27]1

Participants

3

Reactant 2

HCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanoneHCID 89239118HCID 89239118, compound

Product 1

HCID 58190549HCID 58190549, compoundYield 75.9%

Procedure

The title compound (37.0 mg, 70%) was synthesized from 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (15.4) (40.0 mg, 0.12 mmol) and (S)—O-pyrrolidin-3-yl-hydroxylamine hydrochloride (30.0 mg, 0.17 mmol) using the same procedure as described in the synthesis of example 15. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.30 (s, 1H), 8.92 (dd, 1H), 8.41 (dd, 1H), 8.18 (d, 1H), 7.82 (d, 1H), 7.53 (dd, 1H), 6.23 (s, 2H), 4.95 (m, 1H), 3.16-2.87 (m, 3H), 2.77-2.71 (m, 1H), 2.25 (s, 3H), 2.01-1.87 (m, 2H). LCMS (method A): [MH]+=407, tR=3.09 min.

Workup

  1. customas described in the synthesis of example 15

Sources & evidence

ORD record
ord-6df3a35219704518bcb1bccb40cfb80e
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

Loading…