Methylhydrazine → HCID 178462416, compound

HRID 1937160Notes

Reaction equation

HRID 1937160 reaction equation
[CH3:1][NH:2]N.[C:4]([C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[CH:14]=[CH:15]/[C@H:16]2[O:21][CH2:20][C@H:19]([S:22][C@H:23]([CH3:55])[C@@:24]([O:39][C:40](=[O:54])[CH2:41][CH2:42][N:43]3C(=O)C4C(=CC=CC=4)C3=O)([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[F:38])[CH2:25][N:26]3[CH:30]=NC=[N:27]3)[CH2:18][O:17]2)=[C:8]([F:56])[CH:7]=1)#[N:5]>ClCCl>[C:4]([C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[CH:14]=[CH:15]/[C@H:16]2[O:21][CH2:20][C@H:19]([S:22][C@H:23]([CH3:55])[C@@:24]([O:39][C:40](=[O:54])[CH2:41][CH2:42][NH2:43])([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[F:38])[CH2:25][N:26]3[CH:30]=[CH:1][N:2]=[N:27]3)[CH2:18][O:17]2)=[C:8]([F:56])[CH:7]=1)#[N:5]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 178462424HCID 178462424, compound

Product 1

HCID 178462416HCID 178462416, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

222.7 mg (4.38 mmol) of methylhydrazine were added to a solution of 100 mg (0.13 mmol) of [(1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadien-1-yl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propyl]3-(1,3-dioxo-1,3-dihydro-2-isoindolyl)propionate [prepared as described in Step 13(i) above] in 2 ml of dichloromethane in an ice bath. The resulting mixture was stirred at ambient temperature for 20 hours. At the end of this time, the reaction mixture was concentrated and then evaporated to dryness in vacuo. Dichloromethane was added to the resulting residue and the dichloromethane was then evaporated under reduced pressure. The resulting residue was then dissolved in dichloromethane, the solution was allowed to stand at ambient temperature for 12 hours and then concentrated. The residue thus obtained was purified by chromatography on a silica gel (15 g) column using a 9:1 mixture of ethyl acetate and methanol to give 41.5 mg (yield 50%) of the title compound as a pale yellow non-crystalline solid.

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated
  2. customevaporated to dryness in vacuo
  3. additionDichloromethane was added to the resulting residue
  4. customthe dichloromethane was then evaporated under reduced pressure
  5. dissolutionThe resulting residue was then dissolved in dichloromethane
  6. waitto stand at ambient temperature for 12 hours
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. customwas purified by chromatography on a silica gel (15 g) column
  10. additiona 9:1 mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-2c4e33ee8a8b41d3bc86692ceb8ec7e2
Source dataset
uspto-grants-2002_05
Patent number
US06392082B1

Reaction notes

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