HCID 49868763, compound → HCID 49870791, compound

HRID 405997Notes

Reaction equation

HRID 405997 reaction equation
FC1C=C(C2C(=O)C3C(=CC=C(F)C=3)NC=2[C@@H](N2C(=O)C3C(=CC=CC=3)C2=O)C)C=C(F)C=1.[NH2:34][C:35]1[C:40]([C:41]#[N:42])=[C:39]([NH:43][CH:44]([C:46]2[N:47](C)[C:48]3[C:53]([C:54](=[O:64])[C:55]=2[C:56]2[CH:61]=[C:60]([F:62])[CH:59]=[C:58]([F:63])[CH:57]=2)=[CH:52][C:51]([F:65])=[CH:50][CH:49]=3)[CH3:45])[N:38]=[CH:37][N:36]=1>>[NH2:34][C:35]1[C:40]([C:41]#[N:42])=[C:39]([NH:43][C@H:44]([C:46]2[NH:47][C:48]3[C:53]([C:54](=[O:64])[C:55]=2[C:56]2[CH:61]=[C:60]([F:62])[CH:59]=[C:58]([F:63])[CH:57]=2)=[CH:52][C:51]([F:65])=[CH:50][CH:49]=3)[CH3:45])[N:38]=[CH:37][N:36]=1

Participants

3

Reactant 2

HCID 49868763HCID 49868763, compoundHCID 66831363HCID 66831363, compound

Product 1

HCID 49870791HCID 49870791, compound

Procedure

4-amino-6-(((1S)-1-(3-(3,5-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-2-quinolinyl)ethyl)amino)-5-pyrimidinecarbonitrile was synthesized from (S)-2-(1-(3-(3,5-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-2-yl)ethyl)-isoindoline-1,3-dione in a similar manner as the above compound 4-amino-6-(1-(3-(3,5-difluorophenyl)-6-fluoro-1-methyl-4-oxo-1,4-dihydroquinolin-2-yl)-ethylamino)pyrimidine-5-carbonitrile. 1H-NMR (400 Hz, DMSO-d6) δ 11.50 (s, 1H), 7.97 (s, 1H), 7.69-7.73 (m, 2H), 7.59 (td, J=8.0, 4.0 Hz, 1H), 7.46 (s, br, 1H), 7.17-7.22 (m, 2H), 7.05 (s, br, 1H), 5.01-5.06 (m, 1H), 1.48 (t, J=8.0 Hz, 3H). Mass Spectrum (ESI) m/e=437 (M+1).

Sources & evidence

ORD record
ord-bb826bd2d3f74e74a721d8d091dfa128
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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