Nevirapine → HCID 19427675, compound

HRID 1078540Notes

Reaction equation

HRID 1078540 reaction equation
[CH:1]1([N:4]2[C:10]3[N:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=O)[NH:7][C:6]3[C:16]([CH3:20])=[CH:17][CH:18]=[N:19][C:5]2=3)[CH2:3][CH2:2]1.[CH:21]([N:24](C(C)C)CC)(C)C>C(Cl)Cl>[C:21]([C:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[N:11][C:10]=2[N:4]([CH:1]2[CH2:3][CH2:2]2)[C:5]2[N:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:6]=2[N:7]=1)#[N:24]

Participants

4

Reactant 2

HCID 4463NevirapineHCID 81531Diisopropylethylamine

Product 1

HCID 19427675HCID 19427675, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonie anhydride (5.02 g, 17.8 mmole) was added dropwise to a cooled mixture of 3.00 g (11.3 mmole) of 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one, 2.32 g (18.0 mmole) of diisopropylethylamine, and 45 mL of methylene chloride. After the addition was complete, the ice bath was removed and the mixture was stirred for one hour. Ethyl acetate (500 mL) was added and the resulting solution was washed with three 100 mL portions of water. The organic solution was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was chromatographed over silica gel (eluted with 50% ethyl acetate/hexane) to provide 3.18 g (8.0 mmole) of the title compound as a yellow oil, suitable for the next reaction.

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. additionEthyl acetate (500 mL) was added
  4. washthe resulting solution was washed with three 100 mL portions of water
  5. dry with materialThe organic solution was dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed over silica gel (eluted with 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-23e47ab562a34e568535cef6adc8c7ee
Source dataset
uspto-grants-1996_08
Patent number
US05550117

Reaction notes

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