Tetrabutylammonium Fluoride → HCID 44201001, compound

HRID 563229Notes

Reaction equation

[Si]([O:8][C@H:9]([CH3:34])[C@@H:10]([NH:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([Cl:32])[C:25]=1[CH3:33])[C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:14][N:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[Cl:32][C:26]1[C:25]([CH3:33])=[C:24]([NH:23][C@@H:10]([C:11]2[S:12][C:13]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)=[N:14][N:15]=2)[C@H:9]([OH:8])[CH3:34])[CH:31]=[CH:30][C:27]=1[C:28]#[N:29]

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 67006213HCID 67006213, compound

Product 1

HCID 44201001HCID 44201001, compound

Procedure

4-((1R,2R)-2-(tert-butyldimethylsilyloxy)-1-(5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl)propylamino)-2-chloro-3-methylbenzonitrile (347 mg, 0.67 mmol) was deprotected using tetrabutylammonium fluoride (1.0 M solution in THF, 0.8 mL, 0.8 mmol) in a procedure analogous to that used for the preparation of example 7. After column chromatography (50% EtOAc/hexanes) the title compound was isolated as a white solid (269 mg, quant). 1H NMR (500 MHz, CDCl3, δ in ppm) 7.88 (m, 2H), 7.29 (d, J=8.5 Hz, 1H), 7.13 (m, 2H), 6.63 (d, J=8.7 Hz, 1H), 5.47 (d, J=7.6 Hz, 1H), 4.99 (dd, J=3.4, 7.5 Hz, 1H), 4.49 (m, 1H), 3.09 (br s, 1H), 2.30 (s, 3H), 1.31 (d, J=6.4 Hz, 3H).

Workup

customthat used for the preparation of example 7

Sources & evidence

ORD record: ord-3c01a80091ad49ad8727d98ccf2a3529
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067448B2

Reaction notes

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