Silane, tris(1-methylethyl)- → 2-[(3r)-3-Aminopyrrolidin-1-yl]-5-(1,1-dioxido-3-oxo-2,3-dihydro-isothiazol-5-yl)-benzaldehyde

HRID 724596Notes

Reaction equation

C([N:5]1[C:9](=[O:10])[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:21][CH2:20][C@@H:19]([NH:22]C(=O)OC(C)(C)C)[CH2:18]3)=[C:13]([CH:30]=[O:31])[CH:12]=2)[S:6]1(=[O:33])=[O:32])(C)(C)C.C([SiH](C(C)C)C(C)C)(C)C>C(O)(C(F)(F)F)=O>[NH2:22][C@@H:19]1[CH2:20][CH2:21][N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:7]3[S:6](=[O:33])(=[O:32])[NH:5][C:9](=[O:10])[CH:8]=3)=[CH:12][C:13]=2[CH:30]=[O:31])[CH2:18]1

Participants

Conditions

Temperature: 130 °C

Procedure

22-C (63 mg, 0.13 mmol) in TFA (0.65 mL) was treated with triisopropylsilane (0.8 μL, 0.004 mmol). The solution was sealed in a microwave tube and heated to 130° C. for 15 min. The solution was concentrated in vacuo. The residue was purified by reverse phase HPLC to afford a yellow solid (10 mg, 17%). 1H NMR (500 MHz, CD3OD): δ 10.04 (s, 1H), 8.31 (d, J=2.44 Hz, 1H), 7.97 (dd,J=11.2, 2.4 Hz, 1H), 7.14 (d, J=9.27 Hz, 1H), 4.05 (m, 1H), 3.80–3.75 (m, 2H), 3.65–3.47 (m, 2H), 2.52 (m, 1H), 2.22 (m, 1H); LCMS found for C14H15N3O4S (M+H)+: m/z=322.

Workup

customThe solution was sealed in a microwave tube
concentrationThe solution was concentrated in vacuo
customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-3f447d38ffa54bc9a1bedd1ea8f3bb73
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141596B2

Reaction notes

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