Sodium hydride → HCID 178462359, compound

HRID 2423258Notes

Reaction equation

HRID 2423258 reaction equation
[H-].[Na+].Cl.[OH:4][C@H:5]([CH3:9])[C:6](=[NH:8])[NH2:7].[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[C:19]([C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)=[O:34])[C:20]([C:22]1[CH:23]=[CH:24][C:25]([F:32])=[C:26]([S:28](Cl)(=[O:30])=[O:29])[CH:27]=1)=[O:21]>C1COCC1>[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[C:19]([C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=1)=[O:34])[C:20]([C:22]1[CH:23]=[CH:24][C:25]([F:32])=[C:26]([S:28]([NH:8][C:6](=[NH:7])[C@H:5]([OH:4])[CH3:9])(=[O:29])=[O:30])[CH:27]=1)=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 42614222(2R)-2-hydroxypropanimidamide hydrochlorideHCID 1785208725-[2-(1,3-dihydrobenzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]-2-fluorobenzenesulfonyl chloride

Product 1

HCID 178462359HCID 178462359, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

At room temperature, sodium hydride (579 mg) was added to a THF (70 mL) suspension of (2R)-2-hydroxypropanimidamide hydrochloride (1.65 g), followed by heating up to 60° C. and stirring for 30 minutes. The reaction mixture was cooled to room temperature, and a THF (35 mL) solution of 5-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]-2-fluorobenzenesulfonyl chloride (2.10 g) was added, followed by stirring for 20 minutes. Then, this was subjected to liquid-liquid separation with water and ethyl acetate added thereto, the organic layer was washed with saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=50/1) to obtain (2R)-N-({5-[2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-(3-fluorophenyl)-3-oxopropanoyl]-2-fluorophenyl}sulfonyl)-2-hydroxypropanimidamide (1.95 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring for 20 minutes
  3. customThen, this was subjected to liquid-liquid separation with water and ethyl acetate
  4. additionadded
  5. washthe organic layer was washed with saturated brine
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-4e40bef1d99e486991da5572145d4585
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

Loading…