HCID 58190488, compound → HCID 58190485, compound

HRID 1959691Notes

Reaction equation

HRID 1959691 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), δ 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-365f3e89da624525bc44bc4df9c102ed
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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