3,5-Dibromo-1-methylpyridin-2(1H)-one → 5-Bromo-3-(1-ethyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one

HRID 1772096Notes

Reaction equation

HRID 1772096 reaction equation
BrC1N=C(NC2C=CC(C3C(=O)N(C)CCN3C(OC(C)(C)C)=O)=CC=2)C(=O)N(C)C=1.Br[C:33]1[C:34](=[O:41])[N:35]([CH3:40])[CH:36]=[C:37]([Br:39])[CH:38]=1.[CH2:42]([N:44]1[CH:48]=[CH:47][C:46]([NH2:49])=[N:45]1)[CH3:43]>>[Br:39][C:37]1[CH:38]=[C:33]([NH:49][C:46]2[CH:47]=[CH:48][N:44]([CH2:42][CH3:43])[N:45]=2)[C:34](=[O:41])[N:35]([CH3:40])[CH:36]=1

Participants

4

Reactant 3

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 121981091-ethyl-1H-pyrazol-3-amineHCID 86699861tert-Butyl 2-(4-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)-4-methyl-3-oxopiperazine-1-carboxylate

Product 1

HCID 666347205-Bromo-3-(1-ethyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one

Procedure

Following the same general procedure as described for 102k, reaction of 3,5-dibromo-1-methylpyridin-2(1H)-one (1.20 g, 4.50 mmol) with 1-ethyl-3-amino-1H-pyrazole 111b (500 mg, 4.50 mmol) gave a 23% (300 mg) yield of 106a as a white solid: mp 165-167° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.00 (d, 1H, J=2.7 Hz), 7.54 (d, 1H, J=2.4 Hz), 7.37 (d, 1H, J=2.4 Hz), 6.05 (d, 1H, J=2.4 Hz), 4.03 (t, 2H, J=7.2 Hz), 3.49 (s, 3H), 1.36 (t, 3H, J=7.2 Hz); MS (ESI+) m/z 298.1 (M+H).

Sources & evidence

ORD record
ord-d188092872a344fab430a1740084b75b
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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