Dicyclohexylcarbodiimide → 2-Methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide

HRID 1036229Notes

Reaction equation

HRID 1036229 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH3:19])[C:8]([C:11]2[CH:16]=[CH:15][N+:14]([O-:17])=[C:13]([CH3:18])[CH:12]=2)=[N:9][CH:10]=1)([OH:3])=O.[N:20]1[CH:25]=[CH:24][N:23]=[CH:22][C:21]=1[C:26]1[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:18][C:13]1[CH:12]=[C:11]([C:8]2[C:7]([CH3:19])=[CH:6][C:5]([CH2:4][C:1](=[O:3])[NH:32][C:29]3[CH:28]=[CH:27][C:26]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][N:20]=4)=[CH:31][N:30]=3)=[CH:10][N:9]=2)[CH:16]=[CH:15][N+:14]=1[O-:17]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 592592255-(Pyrazin-2-yl)pyridin-2-amineHCID 671347314-(5-(Carboxymethyl)-3-methylpyridin-2-yl)-2-methylpyridine 1-oxide

Product 1

HCID 584479182-Methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(5-(carboxymethyl)-3-methylpyridin-2-yl)-2-methylpyridine 1-oxide 156-6 from Step 4 (0.41 mmol), 5-(pyrazin-2-yl)pyridin-2-amine 86-3 (141 mg, 0.82 mmol), 1,3-dicyclohexylcarbodiimide (188 mg, 0.90 mmol) and 4-(dimethylamino)pyridine (16 mg, 0.16 mmol) in DMF (2 mL) was stirred at room temperature for 10 hours. The crude product was filtered to remove the insoluble and the filtrate was purified by reverse phase HPLC to give 2-methyl-4-(3-methyl-5-(2-oxo-2-(5-(pyrazin-2-yl)pyridin-2-ylamino)ethyl)pyridin-2-yl)pyridine 1-oxide 156 as white solid. MS m/z 413.2 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 11.12 (s, 1H), 9.31 (d, 1H), 9.11 (d, 1H), 8.72 (m, 1H), 8.62 (d, 1H), 8.52 (dd, 1H), 8.48 (d, 1H), 8.31 (d, 1H), 8.21 (d, 1H), 7.73 (m, 2H), 7.52 (dd, 1H), 3.86 (s, 2H), 2.41 (s, 3H), 2.40 (s, 3H).

Workup

  1. filtrationThe crude product was filtered
  2. customto remove the insoluble and the filtrate
  3. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-5f2cc6036f3749b78e93da05f634060b
Source dataset
uspto-grants-2013_10
Patent number
US08546396B2

Reaction notes

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