(Diethylamino)sulfur trifluoride → HCID 71666962, compound

HRID 1055760Notes

Reaction equation

HRID 1055760 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([N:18]2[C:25]3[N:21]([N:22]=[C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=3)[CH:20]=[CH:19]2)=[CH:13][C:12]=1[NH:32][C:33](=[O:50])[C:34]1[CH:39]=[C:38]([S:40]([F:45])([F:44])([F:43])([F:42])[F:41])[CH:37]=[C:36]([C:46](O)([CH3:48])[CH3:47])[CH:35]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([N:18]2[C:25]3[N:21]([N:22]=[C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:24]=3)[CH:20]=[CH:19]2)=[CH:13][C:12]=1[NH:32][C:33](=[O:50])[C:34]1[CH:39]=[C:38]([S:40]([F:45])([F:44])([F:43])([F:42])[F:41])[CH:37]=[C:36]([C:46]([F:7])([CH3:48])[CH3:47])[CH:35]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 71666961HCID 71666961, compound

Product 1

HCID 71666962HCID 71666962, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

At −78° C., a solution of 27 μl (0.203 mmol) of diethylaminosulphur trifluoride (DAST) in 0.5 ml of anhydrous dichloromethane was added to a solution of 100 mg (0.169 mmol) of the compound of Example 148 in 3.5 ml of anhydrous dichloromethane. After the reaction mixture had been stirred at −78° C. for 1 h, 1 ml of saturated aqueous sodium bicarbonate solution was added and the mixture was warmed to RT. Using an Extrelut cartridge NT3 (from Merck, Darmstadt, Germany), the mixture was freed from salts and aqueous components. After concentration, the residue obtained was separated into its components by preparative HPLC (Method 36). Evaporation of the product fractions and drying of the residue under high vacuum gave 50 mg (50% of theory) of the title compound.

Workup

  1. temperaturethe mixture was warmed to RT
  2. concentrationAfter concentration
  3. customthe residue obtained
  4. customwas separated into its components by preparative HPLC (Method 36)
  5. customEvaporation of the product fractions
  6. customdrying of the residue under high vacuum

Sources & evidence

ORD record
ord-ac19a553553140dc94f8abd45c5c3d94
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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