Dimethylformamide → HCID 178456572, compound

HRID 892101Notes

Reaction equation

HRID 892101 reaction equation
Cl.Cl.NC[CH:5]1[CH2:16][N:15]2[C:7]([C:8]3[NH:9][C:10]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:11][C:12]=3[N:13]([CH2:18][CH2:19][CH3:20])[C:14]2=[O:17])=[N:6]1.CO[CH:28]1[CH2:32][CH2:31][CH:30](OC)O1.[CH3:35][N:36](C)C=O>>[CH:21]1([C:10]2[NH:9][C:8]3[C:7]4=[N:6][CH:5]([CH2:30][C:31]5[NH:36][CH:35]=[CH:28][CH:32]=5)[CH2:16][N:15]4[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12]=3[N:11]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 790982,5-DimethoxytetrahydrofuranHCID 178456582HCID 178456582, compound

Product 1

HCID 178456572HCID 178456572, compoundYield 60%

Conditions

Temperature
80 °C

Procedure

Compound 20 (100 mg, 0.26 mmol) obtained in Example 20 and 2,5-dimethoxytetrahydrofuran (67 μL, 0.51 mmol, 2.0 equivalents) were dissolved in N,N-dimethylformamide (2 mL) and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was partitioned with ethyl acetate and water, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. After the organic layer was concentrated, the residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (56 mg, 60%) as a light yellow solid.

Workup

  1. customThe reaction mixture was partitioned with ethyl acetate and water
  2. washthe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationAfter the organic layer was concentrated
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b455a35f8fc843bea7c993b2c502d7fe
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

Loading…