4-(4-Amino-2-fluoro-phenoxy)-6,7-dimethoxy-quinolin-2-ylamine → 1,1-Cyclopropanedicarboxamide

HRID 1924198Notes

Reaction equation

HRID 1924198 reaction equation
NC1C=CC(OC2C3C(=CC(OC)=C(OC)C=3)N=C(N)C=2)=C(F)C=1.COC1C=C2C(=CC=1OC)N=C(SC)C=C2OC1C=CC([NH:48][C:49]([C:51]2([C:54]([NH:56]C3C=CC(F)=CC=3)=[O:55])[CH2:53][CH2:52]2)=[O:50])=CC=1F>>[C:51]1([C:54]([NH2:56])=[O:55])([C:49]([NH2:48])=[O:50])[CH2:53][CH2:52]1

Participants

3

Reactant 2

HCID 578103564-(4-Amino-2-fluoro-phenoxy)-6,7-dimethoxy-quinolin-2-ylamineHCID 57810395N-(4-{[6,7-bis(methyloxy)-2-(methylthio)quinolin-4-yl]oxy}-3-fluorophenyl)-N'-(4-fluoro-phenyl)cyclopropane-1,1-dicarboxamide

Product 1

HCID 2992011,1-Cyclopropanedicarboxamide

Procedure

N-(4-{[2-amino-6,7-bis(methyloxy)quinolin-4-yl]oxy}-3-fluorophenyl)-N′-fluorophenyl)cyclopropane-1,1-dicarboxamide was synthesized from 4-(4-amino-2-fluoro-phenoxy)-6,7-dimethoxy-quinolin-2-ylamine in a similar manner as N-(4-{[6,7-bis(methyloxy)-2-(methylthio)quinolin-4-yl]oxy}-3-fluorophenyl)-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide. It was purified by preparatory HPLC using ammonium acetate and isolated as a white solid (4.0% yield). 1H NMR (DMSO-d6) δ 10.34 (s, 1H), 9.95 (s, 1H), 7.82 (d, 1H), 7.58 (m, 2H), 7.44 (d, 1H), 7.33 (t, 1H), 7.25 (s, 1H), 7.09 (t, 2H), 7.07 (s, 1H), 6.17 (br s, 2H), 5.66 (s, 1H), 3.79 (s, 3H), 3.77 (s, 3H), 1.40 (d, 4H). LCMS: m/z 535 (M+H)+.

Workup

  1. customIt was purified by preparatory HPLC

Sources & evidence

ORD record
ord-fe095f0ccab542be9ad7938ca53e6ce9
Source dataset
uspto-grants-2012_05
Patent number
US08178532B2

Reaction notes

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