HCID 58190488, compound → HCID 58190485, compound

HRID 1892353Notes

Reaction equation

HRID 1892353 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[C:16]4=[N:17][C:18]([C:21](=O)[CH3:22])=[CH:19][N:20]=[C:15]4[N:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH:24][CH2:25][CH:26]([O:29][N:30]1C(=O)C2C(=CC=CC=2)C1=O)[CH2:27][OH:28]>>[OH:24][CH2:25][CH:26]([O:29]/[N:30]=[C:21](/[C:18]1[N:17]=[C:16]2[N:12]([CH2:11][C:7]3[CH:6]=[C:5]4[C:10](=[CH:9][CH:8]=3)[N:1]=[CH:2][CH:3]=[CH:4]4)[N:13]=[N:14][C:15]2=[N:20][CH:19]=1)\[CH3:22])[CH2:27][OH:28]

Participants

3

Reactant 2

HCID 58190488HCID 58190488, compound2×HCID 593418021-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

Product 1

HCID 58190485HCID 58190485, compoundYield 54%

Procedure

The title compound was prepared from 1-(1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone (22.4) and 2-(aminooxy)propane-1,3-diol (intermediate B) in 54% yield using the same procedure as described in the synthesis of example 22 and example 7A. 1H-NMR (400 MHz, CD3OD), 5 ppm 9.40 (s, 1H), 8.86 (dd, 1H), 8.38 (d, 1H), 8.05 (m, 2H), 7.90 (dd, 1H), 7.56 (dd, 1H), 6.22 (s, 2H), 4.46 (t, 1H), 3.87 (d, 4H), 2.42 (s, 3H). LCMS (method B): [MH]+=394, tR=1.86 min.

Workup

  1. customas described in the synthesis of example 22 and example 7A

Sources & evidence

ORD record
ord-d40f10cc8aef474c957f9990d6470d8f
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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