Hydroxyamine hydrochloride → HCID 136062022, compound

HRID 1959765Notes

Reaction equation

HRID 1959765 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.[NH2:26][OH:27]>>[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=[N:20][C:19](/[C:22](=[N:26]/[OH:27])/[CH3:23])=[CH:18][N:17]=[C:16]2[N:15]=[N:14]1

Participants

3

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

Product 1

HCID 136062022HCID 136062022, compoundYield 65%

Procedure

The title compound (68.0 mg, 62%) was synthesized from 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (15.4) (100.0 mg, 0.31 mmol) and hydroxylamine hydrochloride (43.1 mg, 0.62 mmol) using the same procedure as described in the synthesis of example 15. 1H-NMR (400 MHz, DMSO-d6) δ ppm 12.49 (bs, 1H), 9.31 (s, 1H), 8.92 (d, 1H), 8.40 (d, 1H), 8.18 (d, 1H), 7.82 (d, 1H), 7.54 (d, 1H), 6.22 (s, 2H), 2.23 (s, 3H). LCMS (method A): [MH]+=338, tR=5.15 min.

Workup

  1. customas described in the synthesis of example 15

Sources & evidence

ORD record
ord-6de8a94631e34f8a9fec33f840f158aa
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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