Hydrazine hydrate (1:1) → N-[(1S)-2-Amino-1-((4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]-3-chloro-4-[(1-methylethyl)oxy]benzamide

HRID 1785038Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:40]=[CH:41][C:42]=1[O:43][CH:44]([CH3:46])[CH3:45])[C:5]([NH:7][C@@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:29]=[C:30]3[C:35]([CH:36]([OH:38])[CH3:37])=[CH:34][CH:33]=[CH:32][N:31]3[CH:39]=2)=[CH:24][CH:23]=1)[CH2:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)=[O:6].O.NN>C(O)C>[NH2:10][CH2:9][C@@H:8]([NH:7][C:5](=[O:6])[C:4]1[CH:40]=[CH:41][C:42]([O:43][CH:44]([CH3:45])[CH3:46])=[C:2]([Cl:1])[CH:3]=1)[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:29]=[C:30]3[C:35]([CH:36]([OH:38])[CH3:37])=[CH:34][CH:33]=[CH:32][N:31]3[CH:39]=2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 57 °C

Procedure

A mixture of 3-chloro-N-[(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]-4-[(1-methylethyl)oxy]benzamide (2.10 g, 3.30 mmol) and hydrazine monohydrate (0.83 g, 16.5 mmol) in ethanol (30 mL) was heated at 57° C. overnight. The reaction was cooled, diluted with ethanol, filtered, and concentrated to give the title compound (1.67 g, 100%) as a pale yellow powder. MS (ES+) m/e 507 [M+H]+.

Workup

temperatureThe reaction was cooled
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-13830506cd3842dfbbdbd14368e7f92f
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504413B2

Reaction notes

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