Dicyclohexylcarbodiimide → 2-(6-chloro-5-methylpyridin-3-yl)-N-(5-(pyrazin-2-yl)pyridin-2-yl)acetamide

HRID 592152Notes

Reaction equation

HRID 592152 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[CH3:12].[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[N:23][CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH:25][C:22]2[CH:21]=[CH:20][C:19]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][N:13]=3)=[CH:24][N:23]=2)=[O:11])=[CH:4][C:3]=1[CH3:12]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 552673572-(6-Chloro-5-methylpyridin-3-yl)acetic acidHCID 592592255-(Pyrazin-2-yl)pyridin-2-amine

Product 1

HCID 866579532-(6-chloro-5-methylpyridin-3-yl)-N-(5-(pyrazin-2-yl)pyridin-2-yl)acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(6-chloro-5-methylpyridin-3-yl)acetic acid 86-7 (3.0 g, 16.2 mmol), 5-(pyrazin-2-yl)pyridin-2-amine 86-3 (2.80 g, 16.2 mmol), 1,3-dicyclohexylcarbodiimide (4 g, 19.44 mmol) and 4-(dimethylamino)pyridine (324 mg, 3.24 mmol) in DMF (45 mL) was stirred at room temperature for 10 hours. The reaction mixture was filtered to remove the solid and the filtrate was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 5% methanol in dichloromethane to give 2-(6-chloro-5-methylpyridin-3-yl)-N-(5-(pyrazin-2-yl)pyridin-2-yl)acetamide 86-8 as pale yellow solid. MS m/z 340.2 (M+1); 1H NMR 400 MHz (DMSO-d6) δ 11.09(s 1H), 9.31(d, 1H, J=1.6 Hz), 9.11(d, 1H, J=1.6 Hz), 8.72(m, 1H), 8.63(m, 1H), 8.51(dd, 1H, J1=8.6 Hz, J2=2.4 Hz), 8.21(m, 2H), 7.76(d, 1H, J=1.6 Hz), 3.82(s, 2H), 2.33(s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the solid
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-371a41f462d94b36b5508838a6ec9f45
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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