Isopropylamine → N-(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)propan-2-amine

HRID 2410588Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH2:21]O)[CH:18]=[CH:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].C([N:32](C(C)C)[CH:33]([CH3:35])[CH3:34])C.CS(Cl)(=O)=O.C(N)(C)C>C(Cl)Cl.C(#N)C.CCOC(C)=O>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[CH2:21][NH:32][CH:33]([CH3:35])[CH3:34])[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

(3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol (100 mg, 0.26 mmol) was dissolved in DCM (2 mL). N-ethyldiisopropylamine (0.090 mL, 0.52 mmol) was added and the mixture was cooled to 0° C. Methanesulfonyl chloride (22 μl, 0.29 mmol) was added and the resulting mixture was stirred at 0° C. for 10 minutes, and then at RT for 2 hours. The reaction mixture was then poured into a solution of isopropylamine (223 μl, 2.60 mmol) in ACN (2 mL) and stirred at RT for 15 hours. It was diluted with EtOAc, washed with water and brine and dried over MgSO4. After concentration under vacuum, the crude product was purified by flash chromatography (silica, cHex/EtOAc containing 1% of TEA) to give the title compound as a colorless oil. HPLC (Method A) Rt 4.25 min (Purity: 97.1%).

Workup

waitat RT for 2 hours
stirringstirred at RT for 15 hours
washwashed with water and brine
dry with materialdried over MgSO4
concentrationAfter concentration under vacuum
customthe crude product was purified by flash chromatography (silica, cHex/EtOAc containing 1% of TEA)

Sources & evidence

ORD record: ord-610e702969ca4518b2948598ac17c5ff
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

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