Tetrabutylammonium Fluoride → HCID 44200999, compound

HRID 1254675Notes

Reaction equation

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

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 67006740HCID 67006740, compound

Product 1

HCID 44200999HCID 44200999, compound

Procedure

4-((1R,2R)-2-(tert-butyldimethylsilyloxy)-1-(5-phenyl-1,3,4-thiadiazol-2-yl)propyl amino)-2-chloro-3-methylbenzonitrile (242 mg, 0.49 mmol) was deprotected using tetrabutylammonium fluoride (1.0 M solution in THF, 0.97 mL, 0.97 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 (182 mg, 97%). 1H NMR (400 MHz, acetone-d6, δ in ppm) 7.96 (m, 2H), 7.51 (m, 4H), 6.85 (d, J=8.8 Hz, 1H), 5.89 (d, J=7.7 Hz, 1H), 5.15 (dd, J=7.6 Hz, 3.91H), 5.03 (d, J=4.4 Hz, 1H), 4.53 (m, 1H), 2.35 (s, 3H), 1.28 (d, J=6.4 Hz, 3H).

Workup

customthat used for the preparation of example 7

Sources & evidence

ORD record: ord-f2f3c1be644a456491673fd661563172
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455525B2

Reaction notes

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