Triethylamine → HCID 178437632, compound

HRID 1482891Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]2)(O)[CH3:9])=[N:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]2)=[CH2:9])=[N:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl trans-4-[1-(5-chloropyrimidin-2-yl)-1-hydroxyethyl]cyclohexanecarboxylate (54 mg, 0.18 mmol) and triethylamine (36 mg, 0.36 mmol) in dichloromethane (2 mL) was added in portions methanesulfonyl chloride (22 mg, 0.2 mmol) at 0° C. for 10 minutes. The mixture was stirred for 3 hours at 0° C. followed by dilution with brine and extraction with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by prep-TLC (ethyl acetate/petroleum ether) to give methyl trans-4-[1-(5-chloropyrimidin-2-yl)ethenyl]cyclohexanecarboxylate. MS ESI calc'd for C14H18ClN2O2 [M+H]+ 281. found 281. 1H NMR: (400 MHz, CDCl3) δ 8.64 (s, 2H), 6.37 (s, 1H), 5.47 (s, 1H), 3.68 (s, 3H), 2.99-2.96 (m, 1H), 2.37-2.34 (m, 1H), 2.08-1.96 (m, 4H), 1.66-1.60 (m, 2H), 1.34-1.25 (m, 2H).

Workup

extractionfollowed by dilution with brine and extraction with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by prep-TLC (ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-d7d3fdff18554765949f08e56aa8ac9d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416111B2

Reaction notes

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