Dichloromethane → HCID 86687544, compound

HRID 1473489Notes

Reaction equation

HRID 1473489 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[O:22][CH3:23])=[CH:9][CH:8]=[C:7]([S:24]([N:27](CC1C=CC(OC)=CC=1)[C:28]1[S:29][CH:30]=[CH:31][N:32]=1)(=[O:26])=[O:25])[CH:6]=2.C(Cl)Cl.C(O)(C(F)(F)F)=O>CO>[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:13]=1[O:22][CH3:23])=[CH:9][CH:8]=[C:7]([S:24]([NH:27][C:28]1[S:29][CH:30]=[CH:31][N:32]=1)(=[O:26])=[O:25])[CH:6]=2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86687465HCID 86687465, compound

Product 1

HCID 86687544HCID 86687544, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A round-bottom flask was charged with 3-amino-4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (Intermediate NNNN; 42.59 mg, 0.071 mmol), DCM (1 mL) and TFA (0.5 mL). The mixture was stirred for 1 h, then diluted with MeOH and concentrated. The residue was taken up in DCM and loaded onto a 500-mg SCX-2 ion exchange column (Biotage, LLC). The column was eluted with MeOH, then with 2N ammonia in methanol. The basic fractions were combined and concentrated. The residue was concentrated from DCM to give 3-amino-4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (30 mg, 0.062 mmol, 88% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm=12.72 (br. s., 1H), 8.65 (s, 1H), 8.22 (d, J=2.0 Hz, 1H), 7.59 (dd, J=2.0, 8.9 Hz, 1H), 7.52-7.44 (m, 2H), 7.42-7.35 (m, 1H), 7.24 (d, J=4.7 Hz, 1H), 7.08 (d, J=8.9 Hz, 1H), 6.81 (d, J=4.6 Hz, 1H), 5.62 (s, 2H), 3.75 (s, 3H); m/z (ESI) 481.2 (M+H)+.

Workup

  1. concentrationconcentrated
  2. washThe column was eluted with MeOH
  3. concentrationconcentrated
  4. concentrationThe residue was concentrated from DCM

Sources & evidence

ORD record
ord-b5093895a8b8439e91f807e6f0e6028a
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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