Sodium hydride → HCID 11582332, compound

HRID 1517642Notes

Reaction equation

HRID 1517642 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([NH:14][C:15]([NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][NH:22]4)=[O:16])[CH2:7][C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:29][O:30][CH2:31][CH2:32]Br>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([NH:14][C:15]([NH:17][C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH:20]=[N:21][N:22]4[CH2:32][CH2:31][O:30][CH3:29])=[O:16])[CH2:7][C:8]([CH3:12])([CH3:13])[O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 11617330HCID 11617330, compound

Product 1

HCID 11582332HCID 11582332, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 65D (500 mg, 1.41 mmol) in DMF (7 mL) was treated with 60% sodium hydride (68 mg, 1.7 mmol) at room temperature, and the mixture was stirred at this temperature for 1 hour. Bromoethyl methyl ether (0.15 mL, 1.6 mmol) was then added, and the mixture was stirred overnight at room temperature. After this time, most of the DMF was evaporated in vacuo, then water (50 mL) was added. The resulting sticky residue was collected by filtration and was then chromatographed on silica gel (98:2 CH2Cl2—CH3OH) to afford the title compound, 131 mg (23%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.73 (s, 1H), 8.07 (s, 1H), 7.69 (d, J=6.44 Hz, 1H), 7.32 (dd, J=15.09, 7.63 Hz, 1H), 7.18-7.26 (m, 2H), 6.71-6.79 (m, 2H), 6.61 (dd, J=10.85, 2.71 Hz, 1H), 4.96 (m, 1H), 4.51 (t, J=5.43 Hz, 2H), 3.75 (t, J=5.43 Hz, 2H), 3.18 (s, 3H), 2.20 (dd, J=13.39, 6.27 Hz, 1H), 1.78 (dd, J=13.05, 11.02 Hz, 1H), 1.41 (s, 3H), 1.30 (s, 3H). MS (ESI+) m/z 413 (M+H), 435 (M+Na).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. customAfter this time, most of the DMF was evaporated in vacuo
  3. additionwater (50 mL) was added
  4. filtrationThe resulting sticky residue was collected by filtration
  5. customwas then chromatographed on silica gel (98:2 CH2Cl2—CH3OH)

Sources & evidence

ORD record
ord-888517d0523641aa9e7ebbc8a5d416a4
Source dataset
uspto-grants-2012_07
Patent number
US08232309B2

Reaction notes

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