Tetrahydrofuran → HCID 59829889, compound

HRID 1947204Notes

Reaction equation

HRID 1947204 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[C:8]([CH2:15][C:16]#[C:17][CH3:18])=[CH:7][C:6]=1[C:19](=[N:33][NH2:34])[NH:20][C:21]1[CH:26]=[CH:25][C:24](N2CCOCC2)=[CH:23][CH:22]=1)[CH:2]=[CH2:3].[C:35]([N:42]1[CH:46]=[CH:45]N=[CH:43]1)(N1C=CN=C1)=O.[C:47](=[O:50])([O-])[O-].[Na+].[Na+].[O:53]1CCC[CH2:54]1>>[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[C:8]([CH2:15][C:16]#[C:17][CH3:18])=[CH:7][C:6]=1[C:19]1[N:20]([C:21]2[CH:26]=[CH:25][C:24]([CH2:35][N:42]3[CH2:46][CH2:45][O:50][CH2:47][CH2:43]3)=[CH:23][CH:22]=2)[C:54](=[O:53])[NH:34][N:33]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 178458730HCID 178458730, compound

Product 1

HCID 59829889HCID 59829889, compound

Procedure

Crude 2,4-bis-allyloxy-5 (but-2-ynyl)-N-[4-(morpholin-4-yl)-phenyl]-benzene-carbohydrazonamide (F470-IM11: 243 mg) was dissolved in anhydrous tetrahydrofuran (5 mL) and mixed with 1,1′-carbonyldiimidazole (121 mg, 0.75 mmol), and the mixture was stirred for 1.5 hours. The reaction mixture was mixed with saturated sodium carbonate solution (15 mL) and extracted twice with ethyl acetate (30 mL). The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated to obtain the crude title compound (F470-IM12: 208 mg).

Workup

  1. extractionextracted twice with ethyl acetate (30 mL)
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ec889ecd0741490bb02653b2ce5b275b
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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