O-Methylhydroxylamine hydrochloride → HCID 58190561, compound

HRID 1892340Notes

Reaction equation

HRID 1892340 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.[CH3:26][O:27][NH2:28]>>[CH3:26][O:27]/[N:28]=[C:22](/[C:19]1[N:20]=[C:21]2[N:13]([CH2:12][C:3]3[CH:4]=[C:5]4[C:10](=[CH:11][C:2]=3[F:1])[N:9]=[CH:8][CH:7]=[CH:6]4)[N:14]=[N:15][C:16]2=[N:17][CH:18]=1)\[CH3:23]

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

Product 1

HCID 58190561HCID 58190561, compoundYield 70.2%

Procedure

The title compound (22.2 mg, 64%) was synthesized from 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (15.4) (30.0 mg, 0.09 mmol) and O-methyl-hydroxylamine hydrochloride (78.0 mg, 0.93 mmol) using the same procedure as described in the synthesis of example 15. 1H-NMR (400 MHz, CDCl3) δ ppm 9.45 (s, 1H), 8.92 (d, 1H), 8.08 (d, 1H), 7.81 (d, 1H), 7.78 (s, 1H), 7.39 (dd, 1H), 6.16 (s, 2H), 4.13 (s, 3H), 2.33 (s, 3H). LCMS (method E): [MH]+=352, tR=5.43 min.

Workup

  1. customas described in the synthesis of example 15

Sources & evidence

ORD record
ord-0980a3cc75474cd6a2550c03e8778ac2
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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