Hydrochloric Acid → HCID 178436724, compound

HRID 1192516Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:28]([O:30]C)=[O:29])[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[C:6](/[N:14]=[N:15]/[N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:7]=1[C:8]#[C:9][Si](C)(C)C.[OH-].[Na+].Cl>CO.O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:28]([OH:30])=[O:29])[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)=[C:6](/[N:14]=[N:15]/[N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:7]=1[C:8]#[CH:9]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of methyl 4-chloro-6-[(1E)-3,3-diethyltriaz-1-en-1-yl]-3′-fluoro-5-[(trimethylsilyl)ethynyl]biphenyl-2-carboxylate (3.3 g, 7.1 mmol) in methanol (11 mL) and tetrahydrofuran (11 mL) was treated with 1 M sodium hydroxide in water (29 mL, 29 mmol) dropwise and heated at 65° C. for 1 hour. The reaction mixture was cooled to 0° C. and treated with 3 M hydrogen chloride in water (12 mL, 36 mmol) dropwise. This mixture was poured into 1 M hydrogen chloride in water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (50 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product (quantitative). This material was used without further purification. LCMS for C19H18ClFN3O2 (M+H)+: m/z=374.1; Found: 373.9.

Workup

temperatureThe reaction mixture was cooled to 0° C.
extractionextracted with ethyl acetate (2×100 mL)
washThe combined organic extracts were washed with brine (50 mL)
dry with materialdried with sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-374c2ff23fbe461b9d36714c9eb8947d
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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