Methanesulfonyl chloride → HCID 86689554, compound

HRID 1853878Notes

Reaction equation

[NH2:1][C@H:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]3[C:12]4[CH:24]=[CH:23][S:22][C:13]=4[C:14](=[O:21])[NH:15][C:16]=3[CH:17]=[CH:18][C:19]=2[OH:20])=[CH:6][CH:5]=1)[CH3:3].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>>[OH:20][C:19]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:21])[C:13]3[S:22][CH:23]=[CH:24][C:12]=3[C:11]=2[C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([C@@H:2]([NH:1][S:26]([CH3:25])(=[O:28])=[O:27])[CH3:3])=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 86689555HCID 86689555, compound

Product 1

HCID 86689554HCID 86689554, compoundYield 56.3%

Procedure

Following the procedure outlined for Example 301, (S)-9-[4-(1-aminoethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.30 mmol) was reacted with methanesulfonyl chloride (100 mg, 0.89 mmol) to afford the desired product (70 mg, 56%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 5.89-7.55 (m, 2H), 7.52 (d, J=5.4 Hz, 1H), 7.38 (d J=8.9 Hz, 1H), 7.30-7.28 (m, 2H), 7.15 (d, J=8.9 Hz, 1H), 6.00 (d, J=5.4 Hz, 1H), 4.71 (q, J=7.1 Hz, 1H), 2.82 (s, 3H), 1.61 (d, J=7.0 Hz, 3H); ESI MS m/z 415 [C20H18N2O4S2+H]+; HPLC >99% (AUC), tR=12.43 min.

Sources & evidence

ORD record: ord-8000a836b5d84ff7ad0060b073a31764
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962648B2

Reaction notes

Loading…