(5-Fluoro-6-methoxypyridin-3-yl)boronic acid → 4-amino-N-cyclopropyl-7-fluoro-8-(5-fluoro-6-methoxypyridin-3-yl)cinnoline-3-carboxamide

HRID 2375705Notes

Reaction equation

HRID 2375705 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].[F:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[N:25][C:26]=1[O:27][CH3:28]>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:23]3[CH:24]=[N:25][C:26]([O:27][CH3:28])=[C:21]([F:20])[CH:22]=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 44717400(5-Fluoro-6-methoxypyridin-3-yl)boronic acidHCID 672285864-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide

Product 1

HCID 236298564-amino-N-cyclopropyl-7-fluoro-8-(5-fluoro-6-methoxypyridin-3-yl)cinnoline-3-carboxamideYield 61%

Procedure

Using Method A, 4-amino-7-fluoro-8-iodo-N-cyclopropyl-cinnoline-3-carboxamide (175 mg, 0.48 mmol) and 5-fluoro-6-methoxypyridine-3-boronic acid (162 mg, 0.96 mmol) were reacted. After purification the title compound (106 mg, 61% yield) was obtained as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.48 (bm, 1H), 8.15 (m, 1H), 7.92 (a dd, J=5.2, 9.0 Hz, 1H), 7.65 (a d, J=10.7 Hz, 1H), 7.56 (a t, J=9.0 Hz, 1H), 4.10(s, 3H), 2.96 (m, 1H), 0.88 (m, 2H), 0.65 (m, 2H). MS APCI, m/z=372, HPLC 2.59 min.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-c268e580093b4838a259cf18a090ece6
Source dataset
uspto-grants-2008_12
Patent number
US07465795B2

Reaction notes

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