5-(1-Methylpyrrolidin-2-yl)pyridin-2-amine → 5-Bromo-1-methyl-3-(5-(1-methylpyrrolidin-2-yl)pyridin-2-ylamino)pyridin-2(1H)-one

HRID 1919024Notes

Reaction equation

HRID 1919024 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:12]=[CH:13][C:14]3[CH2:15][CH2:16]NC[C:19]=3[CH:20]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.Br[C:22]1[C:23](=O)[N:24](C)[CH:25]=C(Br)C=1.CN1CCCC1C1C=CC(N)=NC=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([CH:15]3[CH2:16][CH2:22][CH2:23][N:24]3[CH3:25])=[CH:13][N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 3

HCID 31107895-(1-Methylpyrrolidin-2-yl)pyridin-2-amineHCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 670162225-Bromo-1-methyl-3-(5,6,7,8-tetrahydro-2,6-naphthyridin-3-ylamino)pyridin-2(1H)-one

Product 1

HCID 580439935-Bromo-1-methyl-3-(5-(1-methylpyrrolidin-2-yl)pyridin-2-ylamino)pyridin-2(1H)-oneYield 81%

Procedure

Using the same general procedure as described for the preparation of 226b, reaction of 3,5-dibromo-1-methylpyridin-2(1H)-one (1.51 g, 5.65 mmol) with 5-(1-methylpyrrolidin-2-yl)-2-amino pyridine (1.00 g, 5.65 mmol) gave an 81% yield (1.65 g) of 229a as a yellow solid: mp 143-145° C.; 1H NMR (300 MHz, DMSO-d6) d 8.73 (s, 1H), 8.68 (d, 1H, J=2.4 Hz), 8.15 (d, 1H, J=2.1 Hz), 7.55 (dd, 1H, J=8.9, 2.1 Hz), 7.52 (s, 1H), 7.30 (d, 1H, J=8.9 Hz), 3.52 (s, 3H), 3.13 (t, 1H, J=7.5 Hz), 2.99 (t, 1H, J=7.5 Hz), 2.19 (m, 1H), 2.10 (m, 1H), 2.05 (s, 3H), 1.79 (m, 2H), 1.71 (m, 1H); MS (ESI+) m/z 363.3 (M+H).

Sources & evidence

ORD record
ord-469577e3316f4a22b22bfeb367da1e80
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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