Dichloromethane → HCID 86687577, compound

HRID 1473520Notes

Reaction equation

HRID 1473520 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=[CH:10][CH:9]=[C:8]([S:21]([N:24](CC1C=CC(OC)=CC=1)[C:25]1[S:26][CH:27]=[CH:28][N:29]=1)(=[O:23])=[O:22])[CH:7]=2)#[N:2].C(Cl)Cl.C(O)(C(F)(F)F)=O>CO>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=[CH:10][CH:9]=[C:8]([S:21]([NH:24][C:25]1[S:26][CH:27]=[CH:28][N:29]=1)(=[O:23])=[O:22])[CH:7]=2)#[N:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86687574HCID 86687574, compound

Product 1

HCID 86687577HCID 86687577, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A vial was charged with 3-cyano-N-(4-methoxybenzyl)-4-(2-methoxyphenyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (23.3 mg, 0.043 mmol), DCM (0.5 mL), and TFA (0.25 mL). After 30 min, the mixture was diluted with MeOH and concentrated, and the crude product was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 0-5% MeOH/DCM) to give 3-cyano-4-(2-methoxyphenyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (13.6 mg, 0.032 mmol, 75.0% yield) as a light-yellow solid. 1H NMR (400 MHz, DMSO-d6) δ=12.99 (br. s., 1H), 9.35 (s, 1H), 8.50 (d, J=1.8 Hz, 1H), 7.98 (dd, J=1.9, 8.8 Hz, 1H), 7.72 (d, J=8.9 Hz, 1H), 7.67-7.58 (m, 1H), 7.40 (dd, J=1.7, 7.5 Hz, 1H), 7.35-7.28 (m, 2H), 7.21 (dt, J=0.8, 7.5 Hz, 1H), 6.89 (d, J=4.6 Hz, 1H), 3.71 (s, 3H). m/z (ESI) 423.2 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customthe crude product was purified by chromatography on silica gel (12-g Redi-Sep Gold column, 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-ee57606d84f3415c8caf67b85efc2800
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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