3-(Aminooxy)propane-1,2-diol → HCID 58190591, compound

HRID 1959692Notes

Reaction equation

HRID 1959692 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.[NH2:24][O:25][CH2:26][CH:27]([OH:30])[CH2:28][OH:29].OCC(ON1C(=O)C2C(=CC=CC=2)C1=O)CO>>[OH:30][CH:27]([CH2:28][OH:29])[CH2:26][O:25]/[N:24]=[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]

Participants

4

Reactant 3

HCID 132730903-(Aminooxy)propane-1,2-diolHCID 58190488HCID 58190488, compoundHCID 593418021-(1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)ethanone

Product 1

HCID 58190591HCID 58190591, compoundYield 40%

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 (3-(aminooxy)propane-1,2-diol) (intermediate B) in 40% yield using the same procedure as described in the synthesis of example 22 and example 7B. 1H-NMR (400 MHz, CD3OD) δ ppm 9.40 (s, 1H), 8.86 (m, 1H), 8.38 (d, 1H), 8.05 (m, 2H), 7.90 (dd, 1H), 7.57 (dd, 1H), 6.23 (s, 2H), 4.45 (m, 1H), 4.34 (m, 1H), 4.01 (m, 1H), 3.63 (m, 2H), 2.41 (s, 3H). LCMS (method B): [MH]+=394, tR=1.96 min.

Workup

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

Sources & evidence

ORD record
ord-12d7dd8a4a6d44d9a31f2d51026bb795
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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