Pyridine → HCID 68530161, compound

HRID 2246554Notes

Reaction equation

[CH3:1][Si:2]([CH3:52])([CH2:41][CH2:42][CH2:43][O:44][Si](CC)(CC)CC)[CH2:3][CH2:4][C:5]1[C:17]2[CH2:16][N:15]3[C:10](=[CH:11][C:12]4[C:22]([O:25][C:26](=[O:35])[O:27][CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)([CH2:23][CH3:24])[C:21](=[O:36])[O:20][CH2:19][C:13]=4[C:14]3=[O:18])[C:9]=2[N:8]=[C:7]2[CH:37]=[CH:38][CH:39]=[CH:40][C:6]=12.F.N1C=CC=CC=1>C(#N)C>[CH2:23]([C:22]1([O:25][C:26](=[O:35])[O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:12]2[CH:11]=[C:10]3[N:15]([C:14](=[O:18])[C:13]=2[CH2:19][O:20][C:21]1=[O:36])[CH2:16][C:17]1[C:5]([CH2:4][CH2:3][Si:2]([CH2:41][CH2:42][CH2:43][OH:44])([CH3:52])[CH3:1])=[C:6]2[CH:40]=[CH:39][CH:38]=[CH:37][C:7]2=[N:8][C:9]3=1)[CH3:24]

Participants

Conditions

Temperature: 21 °C

Procedure

A mixture of Compound 52 (1.70 g, 2.3 mmol), hydrofluoric acid (48% in water, 1.8 mL, 46 mmol), and pyridine (4.5 mL, 55 mmol) in 20 mL of acetonitrile was stirred at 21° C. for 14 hours. The reaction was quenched with saturated sodium bicarbonate solution, and aqueous layer was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to afford yellow oil, which was chromatographed to give the desired product (Yield: 48%).

Workup

customThe reaction was quenched with saturated sodium bicarbonate solution, and aqueous layer
extractionwas extracted with dichloromethane
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated
customto afford yellow oil, which
customwas chromatographed

Sources & evidence

ORD record: ord-92464749ca8048ffbf83f0767ed15427
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687496B2

Reaction notes

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