2,6-Lutidine → N-((1-(2-(1-methylethylsulfonamido)ethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide

HRID 508628Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH2:6][CH2:5]1.N1C(C)=CC=CC=1C.[CH:36]([S:39](Cl)(=[O:41])=[O:40])([CH3:38])[CH3:37].C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:37][CH:36]([S:39]([NH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][NH:11][C:12](=[O:27])[C:13]2[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[C:15]([C:23]([F:24])([F:25])[F:26])[CH:14]=2)[CH2:8][CH2:9]1)(=[O:41])=[O:40])[CH3:38]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of N-((1-(2-aminoethyl)piperidin-4-yl)methyl)-3,5-bis(trifluoromethyl)benzamide (70 mg, 0.18 mmol) and 2,6-lutidine (123 μL, 0.882 mmol) in CH2Cl2 (2 mL) was treated with isopropylsulfonyl chloride (49.9 mg, 0.35 mmol). The reaction was stirred overnight and then transferred to a test tube containing saturated aqueous NaHCO3 (4 mL) and EtOAc (4 mL). The biphasic mixture was mixed vigourously and allowed to separate for 15 min. After separation, the mixture was cooled to −20° C. until the aqueous layer was frozen. The organic layer was then poured off and the solvent was removed under reduced pressure at 50° C. The resulting residue was purified by HiTOPs

Workup

customtransferred to a test tube
additionThe biphasic mixture was mixed vigourously
customto separate for 15 min
customAfter separation
temperaturewas frozen
additionThe organic layer was then poured off
customthe solvent was removed under reduced pressure at 50° C
customThe resulting residue was purified by HiTOPs

Sources & evidence

ORD record: ord-a12308d317fc4170ade14dde01f2c21b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096522B2

Reaction notes

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