HCID 145857648, compound → HCID 21886278, compound

HRID 723234Notes

Reaction equation

C(OC(=O)[NH:7][C:8](=[NH:31])[C:9]1[S:10][C:11]([S:29][CH3:30])=[C:12]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:18]=2)(=[O:16])=[O:15])[CH:13]=1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:30][S:29][C:11]1[S:10][C:9]([C:8]([NH2:31])=[NH:7])=[CH:13][C:12]=1[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH:18]=1)(=[O:16])=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-methylsulfanyl-4-(3-piperidin-1-yl-benzenesulfonyl)-thiophene-2-carboxamidine (10 mg, 0.020 mmol, Example 286: step h) in 1 mL of CH2Cl2 under Ar at 0° C. was added 5 drops (˜200 ul) of TFA. The mixture was stirred at 0° C. for 1 h. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (5% MeOH/CH2Cl2) gave 7.5 mg (77%) of product as colorless oil: 1H-NMR (CD3OD, 400 MHz) δ 8.25 (s, 1H), 7.76 (dd, 1H, J=1.6, 1.6 Hz), 7.62 (ddd, 1H, J=7.5, 1.6, 1.6 Hz), 7.56 (ddd, 1H, J=7.5, 1.6, 1.6 Hz), 7.51 (dd, 1H, J=7.5, 7.5), 3.31–3.30 (m, 4H), 2.54 (s, 3H), 1.57–1.56 (m, 6H). Mass spectrum (ESI, m/z): Calcd. for C17H21N3O2S3, 396.1 (M+H), found 396.2.

Workup

customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record: ord-f572ee11367142cdac2e5fcb9b8f1237
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138530B2

Reaction notes

Loading…