Sodium hydride → HCID 44415998, compound

HRID 2264275Notes

Reaction equation

HRID 2264275 reaction equation
[CH:1]1([NH:7][C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[N:18][CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl>CN(C=O)C>[CH:1]1([NH:7][C:8]2[N:13]=[C:12]([C:14]3[C:22]4[C:17](=[N:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])[CH:15]=3)[CH:11]=[CH:10][N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 44415977HCID 44415977, compound

Product 1

HCID 44415998HCID 44415998, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

Compound 13 (25 mg) was dissolved in DMF (1 mL) and NaH (5 mg) was added. The mixture was stirred for 1 hr, followed by addition of 2-(dimethylamino)ethyl chloride hydrochloride (10 mg). After being warmed to 45° C. for 2 hrs, the solution was concentrated and the residue was purified by flash chromatography [silica gel, DCM:MeOH/9.5:0.5] to afford 13 mg (42%) of the desired product. 1H NMR (400 MHz, CDCl3) δ 8.72 (d, 1 H), 8.35 (d, 1 H), 8.18 (d, 1 H), 7.92 (s, 1 H), 7.15 (dd, 1 H), 6.80 (d, 1 H), 5.01 (d, 1 H), 4.45 (t, 2 H), 3.95 (m, 1 H), 2.80 (t, 2 H), 2.32 (s, 6 H), 2.15 (m, 2 H), 1.80 (m, 2 H), 1.70 (m, 2 H), 1.45 (m, 2 H), 1.30 (m, 2 H). MS (ESI) m/z: 365 (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was purified by flash chromatography [silica gel, DCM:MeOH/9.5:0.5]

Sources & evidence

ORD record
ord-959be61ab04845a196d82b166a0550ca
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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