Triethylamine → HCID 58000921, compound

HRID 658042Notes

Reaction equation

HRID 658042 reaction equation
CS(Cl)(=O)=O.[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:46])[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:29]([CH2:42][CH2:43][CH2:44]O)[C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([N:39]([CH3:41])[CH3:40])=[CH:35][CH:34]=2)=[O:31])=[CH:24][CH:23]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[CH2:47]([N:49](CC)[CH2:50]C)[CH3:48].C(NC)C>ClCCl.O>[C:6]([O:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:46])[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:29]([CH2:42][CH2:43][CH2:44][N:49]([CH2:47][CH3:48])[CH3:50])[C:30]([NH:32][C:33]2[CH:34]=[CH:35][C:36]([N:39]([CH3:40])[CH3:41])=[CH:37][CH:38]=2)=[O:31])=[CH:24][CH:23]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12219N-MethylethylamineHCID 31297Methanesulfonyl chlorideHCID 58001108HCID 58001108, compound

Product 1

HCID 58000921HCID 58000921, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

Under ice cooling, methanesulfonyl chloride (0.30 mL, 3.9 mmol) was added to a solution of N-(2-t-butoxycarbonylaminophenyl)-4-[3-(4-dimethylamino phenyl)-1-(3-hydroxypropyl)ureidomethyl]benzamide (Reference Compound No. 13-79, 200 mg, 0.36 mmol) and triethylamine (0.68 mL, 4.9 mmol) in anhydrous dichloromethane (5.0 mL), and then the reaction mixture was stirred for 7 hours. Water (100 mL) was added thereto, the whole was extracted with ethyl acetate (100 mL), and then the organic layer was washed with brine (100 mL). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. Anhydrous dichloromethane (1.0 mL) and ethylmethylamine (0.03 mL, 0.35 mmol) were added to the residue, and then the mixture was stirred at room temperature for 5 hours. Water (50 mL) was added thereto, the whole was extracted with ethyl acetate (50 mL) and then the organic layer was washed with brine (50 mL). After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to give 9.0 mg of the title reference compound as colorless oil. (Yield 4%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (100 mL)
  2. washthe organic layer was washed with brine (100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. stirringthe mixture was stirred at room temperature for 5 hours
  6. extractionthe whole was extracted with ethyl acetate (50 mL)
  7. washthe organic layer was washed with brine (50 mL)
  8. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  11. customto give 9.0 mg of the title reference compound as colorless oil

Sources & evidence

ORD record
ord-81dbf340888c4221bc68188e3762ab96
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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