Methyl Isocyanate → 1-(4-(4-(3-Oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-((dimethylamino)methyl)pyrimidin-2-yl)phenyl)-3-ethylurea

HRID 75470Notes

Reaction equation

[CH:1]12[N:8]([C:9]3[CH:14]=[C:13]([CH2:15][N:16]([CH3:18])[CH3:17])[N:12]=[C:11]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][CH3:29])=[O:27])=[CH:21][CH:20]=4)[N:10]=3)[CH:5]([CH2:6][CH2:7]1)[CH2:4][O:3][CH2:2]2.[CH3:30]N=C=O>>[CH:5]12[N:8]([C:9]3[CH:14]=[C:13]([CH2:15][N:16]([CH3:18])[CH3:17])[N:12]=[C:11]([C:19]4[CH:20]=[CH:21][C:22]([NH:25][C:26]([NH:28][CH2:29][CH3:30])=[O:27])=[CH:23][CH:24]=4)[N:10]=3)[CH:1]([CH2:7][CH2:6]1)[CH2:2][O:3][CH2:4]2

Participants

Reactant 2

HCID 12228Methyl Isocyanate

HCID 66750273HCID 66750273, compound

Product 1

HCID 667503161-(4-(4-(3-Oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-((dimethylamino)methyl)pyrimidin-2-yl)phenyl)-3-ethylureaYield 21%

Procedure

A procedure similar to that used for the preparation of 1-(4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-((dimethylamino)methyl)pyrimidin-2-yl)phenyl)-3-methylurea was used, substituting ethylisocyanate for methylisocyanate, to provide the mono-TFA salt of 1-(4-(4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-((dimethylamino)methyl)pyrimidin-2-yl)phenyl)-3-ethylurea (0.014 g, 21%) as a white solid. MS: 411.4, M+H.

Sources & evidence

ORD record: ord-4fff0e630275408a938de5290bf32cb3
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835429B2

Reaction notes

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