Benzoic Acid → 5-(1-benzoylpyrrolidin-2-yl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

HRID 1473427Notes

Reaction equation

HRID 1473427 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[CH:20]2[CH2:24][CH2:23][CH2:22][NH:21]2)[CH:11]=1)(=[O:9])=[O:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:69](O)(=[O:76])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1>CN(C=O)C.C(OCC)(=O)C>[C:69]([N:21]1[CH2:22][CH2:23][CH2:24][CH:20]1[C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH:18]=[CH:19][C:10]([S:7]([N:6]([CH2:5][C:4]1[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:3]=1[O:2][CH3:1])[C:25]1[S:26][CH:27]=[CH:28][N:29]=1)(=[O:9])=[O:8])=[CH:11]2)(=[O:76])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86687404N-(2,4-dimethoxybenzyl)-5-(pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(2,4-dimethoxybenzyl)-5-(pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (Intermediate NN, 0.033 g, 0.065 mmol) and HBTU (0.037 g, 0.097 mmol) were dissolved in DMF (0.324 mL). Hunig's base (0.034 mL, 0.194 mmol) and benzoic acid (0.016 g, 0.130 mmol) were added and the reaction was stirred for four hours at room temperature. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (12 g silica gel column, gradient elution 0 to 100% EtOAc:Heptane) to afford 5-(1-benzoylpyrrolidin-2-yl)-N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide as an off-white solid. m/z (ESI) 614.3 (M+H)+.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was purified via column chromatography (12 g silica gel column, gradient elution 0 to 100% EtOAc:Heptane)

Sources & evidence

ORD record
ord-71a35fdaa4154de08eb5c2795ad33a25
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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