3,5-Dibromo-1-methylpyridin-2(1H)-one → 5-Bromo-1-methyl-3-(5-(3-methylazetidin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-one

HRID 1919037Notes

Reaction equation

HRID 1919037 reaction equation
BrC1N=C(NC2C=CC(C3CCN(C(OC(C)(C)C)=O)CC3)=CC=2)C(=O)N(C)C=1.[CH3:30][CH:31]1[CH2:34][N:33]([C:35]2[CH:36]=[CH:37][C:38]([NH2:41])=[N:39][CH:40]=2)[CH2:32]1.Br[C:43]1[C:44](=[O:51])[N:45]([CH3:50])[CH:46]=[C:47]([Br:49])[CH:48]=1>>[Br:49][C:47]1[CH:48]=[C:43]([NH:41][C:38]2[CH:37]=[CH:36][C:35]([N:33]3[CH2:34][CH:31]([CH3:30])[CH2:32]3)=[CH:40][N:39]=2)[C:44](=[O:51])[N:45]([CH3:50])[CH:46]=1

Participants

4

Reactant 3

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 580439635-(3-Methylazetidin-1-yl)pyridin-2-amineHCID 58043998tert-Butyl 4-(4-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)piperidine-1-carboxylate

Product 1

HCID 580439105-Bromo-1-methyl-3-(5-(3-methylazetidin-1-yl)pyridin-2-ylamino)pyridin-2(1H)-oneYield 44%

Procedure

Using the same procedure as described for the preparation of 121a, a reaction of 236b (1.04 g, 6.40 mmol) with 3,5-dibromo-1-methylpyridin-2(1H)-one (1.90 g, 7.12 mmol) afforded a 44% yield (980 mg) of 236c as a brown solid: mp 135-136° C.; 1H NMR (500 MHz, DMSO-d6) d 8.49 (d, 1H, J=5.5 Hz), 8.42 (s, 1H), 7.50 (d, 1H, J=4.5 Hz), 7.41 (d, 1H, J=7.0 Hz), 7.20 (d, 1H, J=14.5 Hz), 6.85 (dd, 1H, J=14.5, 5.0 Hz), 3.91 (m, 2H), 3.49 (s, 3H), 3.34 (m, 2H), 2.75 (m, 1H), 1.21 (d, 3H, J=11.5 Hz; MS (ESI+) m/z 350.2 (M+H).

Sources & evidence

ORD record
ord-85900dc367dc48c2bf5e2d2d8db65c03
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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