Methyl iodide → HCID 57550065, compound

HRID 1676218Notes

Reaction equation

HRID 1676218 reaction equation
[H-].[Na+].[O:3]=[C:4]1[CH:9]=[C:8]([O:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:22]=[CH:21][C:20]([CH2:23][CH2:24][CH3:25])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)[CH:7]=[CH:6][N:5]1[C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:28][CH:27]=1.[CH3:39]I>CN(C=O)C>[CH3:39][N:32]([C:29]1[CH:28]=[CH:27][C:26]([N:5]2[CH:6]=[CH:7][C:8]([O:10][CH:11]3[CH2:16][CH2:15][N:14]([C:17]4[N:22]=[CH:21][C:20]([CH2:23][CH2:24][CH3:25])=[CH:19][N:18]=4)[CH2:13][CH2:12]3)=[CH:9][C:4]2=[O:3])=[CH:31][CH:30]=1)[C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57550087HCID 57550087, compound

Product 1

HCID 57550065HCID 57550065, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of sodium hydride (9.1 mg, 0.23 mmol), N-(4-(2-oxo-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-1(2H)-yl)phenyl)pivalamide (15 mg, 0.030 mmol) in DMF (2 mL) was added Methyl iodide (10 μL, 0.16 mmol). The reaction was stirred at room temperature for 1.5 h. The reaction was quenched with H2O and extracted with EtOAc. The organic layer was concentrated in vacuo to a white solid. The solid was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2) to yield 10 mg of the desired product as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.19 (s, 2H), 7.39-7.48 (m, 2H), 7.32-7.39 (m, 2H), 7.26 (d, J=2.01 Hz, 1H), 5.98-6.09 (m, 2H), 4.55-4.64 (m, 1H), 4.16-4.28 (m, 2H), 3.59-3.71 (m, 2H), 3.27 (s, 3H), 2.43 (t, J=7.40 Hz, 2H), 1.98-2.22 (m, 2H), 1.74-1.98 (m, 2H), 1.53-1.66 (m, 2H), 1.12 (s, 9 H), 0.96 (t, J=7.28 Hz, 3H). MS (ESI) 504 (M+H).

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated in vacuo to a white solid
  4. customThe solid was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-1382fa8516e942fc8994d526eac3a9d8
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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