Methanesulfonyl chloride → HCID 67455222, compound

HRID 1853874Notes

Reaction equation

HRID 1853874 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[C:11]4[CH:23]=[CH:22][S:21][C:12]=4[C:13](=[O:20])[NH:14][C:15]=3[CH:16]=[CH:17][C:18]=2[OH:19])=[CH:5][CH:4]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[OH:19][C:18]1[CH:17]=[CH:16][C:15]2[NH:14][C:13](=[O:20])[C:12]3[S:21][CH:22]=[CH:23][C:11]=3[C:10]=2[C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 53386374HCID 53386374, compound

Product 1

HCID 67455222HCID 67455222, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9-[4-(aminomethyl)phenyl]-8-hydroxythieno[2,3-c]quinolin-4(5H)-one (50 mg, 0.16 mmol) and methanesulfonyl chloride (43 mg, 0.37 mmol) in methylene chloride (5 mL) was stirred at room temperature for 10 min. N,N-diisopropylethylamine (48 mg, 0.37 mmol) was added and the reaction mixture was stirred for 1.5 h, concentrated under reduced pressure and the residue was purified by preparatory HPLC (C18 silica, water/acetonitrile w/0.05% TFA gradient) to afford the desired product (28 mg, 45%) as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 11.77 (s, 1H), 9.22 (s, 1H), 7.70-7.67 (m, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.36 (d, J=8.9 Hz, 1H), 7.23 (d, J=8.0 Hz, 2H), 7.15 (d, J=8.9 Hz, 1H), 5.89 (d, J=5.4 Hz, 1H), 4.29 (d, J=6.4 Hz, 2H), 2.94 (s, 3H); ESI MS m/z 401 [C19H16N2O4S+H]+; HPLC >99% (AUC), tR=12.12 min.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by preparatory HPLC (C18 silica, water/acetonitrile

Sources & evidence

ORD record
ord-df05e5c9ff114e549325cc4b25ee71c7
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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