Hydroxyamine hydrochloride → 4-[(3E)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)-1-(2-methylphenyl)propyl]-N-[1-(hydroxymethyl)cyclopropyl]benzamide

HRID 1617853Notes

Reaction equation

[OH:1][CH2:2][C:3]1([NH:6][C:7](=[O:33])[C:8]2[CH:13]=[CH:12][C:11]([CH:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH3:32])[CH2:15][C:16]([C:18]3[CH:23]=[CH:22][C:21](=[O:24])[N:20]([CH3:25])[CH:19]=3)=O)=[CH:10][CH:9]=2)[CH2:5][CH2:4]1.Cl.[NH2:35][OH:36].C(=O)([O-])O.[Na+]>>[OH:36]/[N:35]=[C:16](/[C:18]1[CH:23]=[CH:22][C:21](=[O:24])[N:20]([CH3:25])[CH:19]=1)\[CH2:15][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([C:7]([NH:6][C:3]2([CH2:2][OH:1])[CH2:5][CH2:4]2)=[O:33])=[CH:9][CH:10]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32]

Participants

Reactant 3

HCID 443297Hydroxyamine hydrochloride

HCID 516892Sodium Bicarbonate

HCID 67015716N-(1-(Hydroxymethyl)cyclopropyl)-4-(3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-oxo-1-o-tolylpropyl)benzamide

Product 1

HCID 580433014-[(3E)-3-hydroxyimino-3-(1-methyl-6-oxo-3-pyridinyl)-1-(2-methylphenyl)propyl]-N-[1-(hydroxymethyl)cyclopropyl]benzamide

Procedure

In analogy to example 151, step 3, N-(1-(hydroxymethyl)cyclopropyl)-4-(3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-oxo-1-o-tolylpropyl)benzamide was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound as an off-white solid containing <10% of the corresponding Z isomer, MS (ESI+): m/z=460.4 [M+H]+.

Sources & evidence

ORD record: ord-7305cd3c17324196b4c0a090d5c41943
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765730B2

Reaction notes

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