Triethylamine → HCID 74834218, compound

HRID 2427859Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:37])[C:7]=1[CH:8]=[C:9]([O:28][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:10]1[C:18]2[C:17]3[CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:16]=3[O:15][C:14]=2[C:13]([O:26][CH3:27])=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>C(Cl)Cl.O.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:37])[C:7]=1[CH:8]=[C:9]([O:28][C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:10]1[C:18]2[C:17]3[CH:19]=[C:20]([NH:23][S:46]([CH3:45])(=[O:48])=[O:47])[CH:21]=[CH:22][C:16]=3[O:15][C:14]=2[C:13]([O:26][CH3:27])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Crude benzoic acid 2-(3,5-dichloro-pyridin-4-yl)-1-(4-methoxy-8-amino-dibenzofuran-1-yl)-vinyl ester (1.17 g, obtained as described in Example 8 starting from 1.68 g of benzoic acid 2-(3,5-dichloro-pyridin-4-yl)-1-(4-methoxy-8-nitro-dibenzofuran-1-yl)-vinyl ester) is dissolved in dry DCM (5 mL) under nitrogen atmosphere. The solution is cooled to 0° C. and triethylamine (0.390 mL, 2.80 mmoles) and methanesulphonyl chloride (0.220 mL, 2.83 mmoles) are added sequentially dropwise. The resulting solution is stirred at room temperature for 1 hour. The mixture is diluted with water (2.5 mL) and saturated NaHCO3 solution (10 mL) and extracted with DCM; the combined organic layers are dried over Na2SO4 and evaporated to dryness. The crude is purified by preparative HPLC to yield 330 mg of pure product as a white solid.

Workup

extractionextracted with DCM
dry with materialthe combined organic layers are dried over Na2SO4
customevaporated to dryness
customThe crude is purified by preparative HPLC

Sources & evidence

ORD record: ord-49887ccc4b4641aca2fb3ed0514cdf06
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968724B2

Reaction notes

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