(2,4-Dimethoxypyrimidin-5-yl)boronic acid → 4-amino-N-cyclopropyl-7-fluoro-8-(2,4-dimethoxypyrimidin-5-yl)cinnoline-3-carboxamide

HRID 2375710Notes

Reaction equation

HRID 2375710 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7](I)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:19][CH2:18]1)=[O:15].[CH3:20][O:21][C:22]1[N:27]=[C:26]([O:28][CH3:29])[C:25](B(O)O)=[CH:24][N:23]=1>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:25]3[C:26]([O:28][CH3:29])=[N:27][C:22]([O:21][CH3:20])=[N:23][CH:24]=3)[C:8]([F:12])=[CH:9][CH:10]=2)[N:5]=[N:4][C:3]=1[C:14]([NH:16][CH:17]1[CH2:19][CH2:18]1)=[O:15]

Participants

3

Reactant 2

HCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 672285864-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide

Product 1

HCID 597915554-amino-N-cyclopropyl-7-fluoro-8-(2,4-dimethoxypyrimidin-5-yl)cinnoline-3-carboxamideYield 39.6%

Procedure

Using Method A, 4-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide (178 mg, 0.48 mmol) and 2,4-dimethoxypyrimidin-5-boronic acid (176 mg, 0.96 mmol) were reacted. After purification the title compound (73 mg, 39% yield) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6 ) δ 9.04 (d, J=4.9 Hz, 1H), 8.57 (dd, J=5.6, 9.3 Hz, 1H), 8.37 (s, 1H) 7.77 (t, J=9.1 Hz, 1H), 3.99 (s, 3H), 3.84 (s, 3H), 2.93 (m, 1H), 0.70(m, 4H). MS APCI, m/z=385.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5a19198c0757432d848bdc7425be1b38
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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