Tetrahydrofuran → HCID 57663088, compound

HRID 2200075Notes

Reaction equation

HRID 2200075 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25][CH3:26])[N:6]2[CH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#N)=[CH:19][CH:18]=1.C1C[O:30]CC1>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25][CH3:26])[N:6]2[CH2:16][C:17]1[CH:18]=[CH:19][C:20]([CH:21]=[O:30])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 58019861HCID 58019861, compound

Product 1

HCID 57663088HCID 57663088, compound

Conditions

Temperature
0 °C

Procedure

The product of example 5 (100 mg) is dissolved in dry THF (3 mL) and cooled to 0° C. under argon. The reagent generated in example 6 (0.72 mL) is added to the reaction flask and the mixture is stirred at 0-5° C. for 1 h and then quenched by addition of 3 M HCl. The mixture is then extracted with ethyl acetate and then dichloromethane and concentrated in vacuo to yield 85 mg. NMR is consistent with structure assignment.

Workup

  1. additionis added to the reaction flask
  2. customquenched by addition of 3 M HCl
  3. extractionThe mixture is then extracted with ethyl acetate
  4. concentrationdichloromethane and concentrated in vacuo
  5. customto yield 85 mg

Sources & evidence

ORD record
ord-81f7d1a40efd49ca9420c72f491d77e1
Source dataset
uspto-grants-2016_06
Patent number
US09359360B2

Reaction notes

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