Acetic Acid → N-(2,4-dimethoxybenzyl)-5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

HRID 1473429Notes

Reaction equation

HRID 1473429 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].[O:36]1[CH2:41][CH2:40][C:39](=O)[CH2:38][CH2:37]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[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][N:21]2[CH:39]2[CH2:40][CH2:41][O:36][CH2:37][CH2:38]2)[CH:11]=1)(=[O:9])=[O:8]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 86687404N-(2,4-dimethoxybenzyl)-5-(pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Product 1

HCID 86687474N-(2,4-dimethoxybenzyl)-5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 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 tetrahydro-4h-pyran-4-one (8.97 μl, 0.097 mmol) were dissolved in DCM (0.648 ml). Sodium triacetoxyborohydride (0.041 g, 0.194 mmol) and acetic acid (5.56 μl, 0.097 mmol) were added and the reaction was stirred for three hours at room temperature. 1M sodium hydroxide solution was added followed by ethyl acetate, and the reaction was stirred for one hour. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated to afford crude N-(2,4-dimethoxybenzyl)-5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide as an off-white solid. m/z (ESI) 594.3 (M+H)+.

Workup

  1. stirringthe reaction was stirred for one hour
  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

Sources & evidence

ORD record
ord-40687b04fd4a48fe9a8b2229d525f952
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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