Toluene → HCID 23502856, compound

HRID 1835357Notes

Reaction equation

[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH3:30])[C:8](=[O:29])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([CH:22](O)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[N:11][CH:10]=1.C(N(CC)CC)C.CS([Cl:51])(=O)=O.C1(C)C=CC=CC=1>ClCCl>[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][N:7]([CH3:30])[C:8](=[O:29])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([CH:22]([Cl:51])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[N:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 50 mg (0.090 mmol) (RS)-N-(3,5-bis-trifluoromethyl-benzyl)-6-(1-hydroxy-hexyl)-N-methyl-4-o-tolyl-nicotinamide (Example 77) and 0.032 ml (0.23 mmol) triethylamine in 3 ml dichloromethane was treated with 0.008 ml (0.1 mmol) methanesulfonyl chloride at 0° C. The reaction mixture was stirred at 0° C. for 10 min and then allowed to warm to room temperature. After 1 h 3 ml toluene were added, and the mixture was stirred at 80° C. over night. Cooling to room temperature was followed by dilution with dichloromethane, washing with water, drying with sodium sulfate and concentration. Column chromatography gave 43 mg (83%) of the title compound as a light yellow viscous oil.

Workup

temperatureto warm to room temperature
stirringthe mixture was stirred at 80° C. over night
temperatureCooling to room temperature
washwashing with water
dry with materialdrying with sodium sulfate and concentration

Sources & evidence

ORD record: ord-da2fd57cee5843929e01a45847a30280
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770637B2

Reaction notes

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