Hydrazine hydrate (1:1) → N-[(1R)-2-amino-1-phenylethyl]-8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 64474Notes

Reaction equation

[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:21][C@H:22]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:23][N:24]4C(=O)C5C(=CC=CC=5)C4=O)=[O:20])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>C(O)C>[NH2:24][CH2:23][C@H:22]([NH:21][C:19]([C:15]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:10]2=[N:17][C:16]=1[CH3:18])=[O:20])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 300 mg of 8-(cyclohexylmethoxy)-N-[(1R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-phenylethyl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide in 6 ml of ethanol was added 0.13 ml of hydrazine monohydrate, followed by stirring at 85° C. for 1 hour. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 200 mg of N-[(1R)-2-amino-1-phenylethyl]-8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-4dbd9a9b1fce4ed7a0093afac3d87d5b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447090B2

Reaction notes

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