Trifluoroacetic acid → 5-(1-benzoylpyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

HRID 1473428Notes

Reaction equation

HRID 1473428 reaction equation
[C:1]([N:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18]([S:24]([N:27](CC1C=CC(OC)=CC=1OC)[C:28]1[S:29][CH:30]=[CH:31][N:32]=1)(=[O:26])=[O:25])=[CH:19]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[C:1]([N:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18]([S:24]([NH:27][C:28]1[S:29][CH:30]=[CH:31][N:32]=1)(=[O:26])=[O:25])=[CH:19]2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866874735-(1-benzoylpyrrolidin-2-yl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Product 1

HCID 715866085-(1-benzoylpyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(1-benzoylpyrrolidin-2-yl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (0.040 g, 0.065 mmol) was dissolved in DCM and TFA (0.1 mL, 1.298 mmol) was added. The reaction was stirred for 15 minutes at room temperature. The reaction was diluted with methanol and concentrated. The material was triturated in diethyl ether, filtered, and the solids were washed with diethyl ether. The solids were collected and vacuum dried overnight to afford 5-(1-benzoylpyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=12.79 (br. s., 1H), 8.48 (s, 1H), 8.38 (d, J=8.8 Hz, 1H), 8.11-7.95 (m, 1H), 7.87 (d, J=9.3 Hz, 1H), 7.75-7.57 (m, 4H), 7.49 (br. s., 3H), 7.26 (br. s., 1H), 7.17-6.96 (m, 1H), 6.84 (d, J=4.2 Hz, 1H), 5.94 (br. s., 1H), 3.90 (br. s., 1H), 3.58 (br. s., 1H), 2.70-2.58 (m, 1H), 1.89 (br. s., 2H), 1.74 (br. s., 1H). m/z (ESI) 464.2 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe material was triturated in diethyl ether
  3. filtrationfiltered
  4. washthe solids were washed with diethyl ether
  5. customThe solids were collected
  6. customvacuum dried overnight

Sources & evidence

ORD record
ord-9c0ae448a535476b8e4b0c83100dc42f
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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