4-Bromo-3,5-dimethylpyridine → 8-(Cyclopentyloxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one

HRID 659060Notes

Reaction equation

HRID 659060 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH3:9].[NH2:10][C:11]1[C:20]2[C:15](=[C:16]([O:23][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[NH:14][C:13](=[O:29])[CH:12]=1>>[CH:24]1([O:23][C:16]2[C:17]([O:21][CH3:22])=[CH:18][CH:19]=[C:20]3[C:15]=2[NH:14][C:13](=[O:29])[CH:12]=[C:11]3[NH:10][C:2]2[C:7]([CH3:8])=[CH:6][N:5]=[CH:4][C:3]=2[CH3:9])[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 223232464-Bromo-3,5-dimethylpyridineHCID 667812934-amino-8-(cyclopentyloxy)-7-methoxyquinolin-2(1H)-one

Product 1

HCID 248519148-(Cyclopentyloxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one

Procedure

The title compound was prepared from 4-bromo-3,5-dimethylpyridine and 4-amino-8-(cyclopentyloxy)-7-methoxyquinolin-2(1H)-one (Example 1, Step 6) following the procedure outlined in Example 8. 1H NMR (400 MHz, DMSO-d6): δ 9.08 (s, 1H), 8.44 (s, 1H), 8.40 (s, 2H), 7.88 (d, 1H), 7.03 (d, 1H), 4.96 (m, 1H), 4.51 (s, 1H), 3.90 (s, 3H), 2.13 (s, 6H), 1.80-1.54 (m, 8H); MS (ESI): 380.2.

Sources & evidence

ORD record
ord-2964589d2eaa4b208e00e12b95900403
Source dataset
uspto-grants-2011_12
Patent number
US08080563B2

Reaction notes

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