Acetohydrazide → HCID 71699927, compound

HRID 456169Notes

Reaction equation

HRID 456169 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.[C:25]([NH:28][NH2:29])(=[O:27])[CH3:26]>>[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](=[N:29]/[NH:28][C:25](=[O:27])[CH3:26])/[CH3:23])[N:20]=2)[N:15]=[N:14]1

Participants

3

Reactant 2

HCID 14039AcetohydrazideHCID 581905781-[3-(7-Fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone

Product 1

HCID 71699927HCID 71699927, compoundYield 89.6%

Procedure

The title compound (30.5 mg, 82%) was synthesized from 1-[3-(7-fluoro-quinolin-6-ylmethyl)-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl]-ethanone (30.0 mg, 0.09 mmol) and acetic acid hydrazide (23.0 mg, 0.28 mmol) using the same procedure as described in the synthesis of example 72. 1H-NMR (400 MHz, DMSO-d6) δ ppm 10.83 (bs, 1H), 9.46 (s, 1H), 8.93 (dd, 1H), 8.40 (d, 1H), 8.19 (d, 1H), 7.81 (d, 1H), 7.53 (dd, 1H), 6.22 (s, 2H), 2.34, 2.14 (s, 6H). LCMS (method A): [MH]+=379, tR=2.07 min.

Workup

  1. customas described in the synthesis of example 72

Sources & evidence

ORD record
ord-e03145c533aa40f7a38eaec358fc1f04
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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