1,1-Dimethylhydrazine → HCID 59750706, compound

HRID 748851Notes

Reaction equation

HRID 748851 reaction equation
C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[CH3:20][N:21]([CH3:23])[NH2:22].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH:34]([C:44]2[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=2[F:51])[C:35]2[N:40]=[CH:39][C:38]([C:41](O)=[O:42])=[CH:37][CH:36]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1>CN(C)C1C=CN=CC=1.ClCCl.CO>[CH3:20][N:21]([CH3:23])[NH:22][C:41](=[O:42])[C:38]1[CH:37]=[CH:36][C:35]([CH:34]([S:31]([C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=2)(=[O:32])=[O:33])[C:44]2[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=2[F:51])=[N:40][CH:39]=1

Participants

8

Reactant 4

HCID 59761,1-DimethylhydrazineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23114724[6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid

Product 1

HCID 59750706HCID 59750706, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (32 μl, 0.23 mmol), 4-dimethylaminopyridine (12 mg, 0.095 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (44 mg, 0.23 mmol) and 1,1-dimethylhydrazine (21 μl, 0.23 minol) were added to the [6-[(4-chlorophenylsulfonyl) (2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid (80 mg, 0.19 mmol), which had been obtained in Example 338, in dichloromethane (5 ml). The resulting mixture was stirred at room temperature for 7 hours. The reaction mixture was diluted with dichloromethane, followed by successive washing with water, a saturated aqueous solution of sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column and a fraction obtained from the elution portion with dichloromethane:methanol =50:1 was concentrated under reduced pressure, whereby the title compound (60 mg, 0.13 mmol, 68%) was obtained as a colorless amorphous substance.

Workup

  1. washby successive washing with water
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customa fraction obtained from the elution portion with dichloromethane

Sources & evidence

ORD record
ord-2aad7cf1d73c4aeea28945b8bfb66679
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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