Hydrazine hydrate (1:1) → N1-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl) propane-1,3-diamine

HRID 1921994Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([NH:34][CH3:35])[N:29]=3)[CH:9]=[C:10]2[NH:13][CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][CH:4]=1.O.NN>C(O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:28]3[CH:33]=[CH:32][N:31]=[C:30]([NH:34][CH3:35])[N:29]=3)[CH:9]=[C:10]2[NH:13][CH2:14][CH2:15][CH2:16][NH2:17])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(3-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl) amino)propyl)isoindoline-1,3-dione 181 (95 mg) in ethanol (10 ml) was added hydrazine hydrate (0.1 ml) and the mixture stirred at 80° C. 3 hours. After cooling the mixture in an ice bath the precipitate formed was filtered off and washed with ice cold ethanol. The filtrate was evaporated to dryness to yield N1-(7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl) propane-1,3-diamine 182 as a yellow solid which was used in the next step without further purification.

Workup

custom3 hours
temperatureAfter cooling the mixture in an ice bath the precipitate
customformed
filtrationwas filtered off
washwashed with ice cold ethanol
customThe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-41496f655fb34a70bba45e41c112448f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173808B2

Reaction notes

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