Ethyl Acetate → N-[4-(Aminosulfonyl)-2-methylphenyl]-7-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxamide

HRID 1519405Notes

Reaction equation

HRID 1519405 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][CH3:15])=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([OH:19])=O)[C:9](=[O:16])[O:10]2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.CCCP(=O)=O.C(OCC)(=O)C.[NH2:41][C:42]1[CH:47]=[CH:46][C:45]([S:48]([NH2:51])(=[O:50])=[O:49])=[CH:44][C:43]=1[CH3:52]>C(Cl)Cl>[NH2:51][S:48]([C:45]1[CH:46]=[CH:47][C:42]([NH:41][C:17]([C:8]2[C:9](=[O:16])[O:10][C:11]3[C:6]([CH:7]=2)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:12]=3[CH2:13][CH2:14][CH3:15])=[O:19])=[C:43]([CH3:52])[CH:44]=1)(=[O:49])=[O:50]

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1430374-Amino-3-methylbenzene-1-sulfonamideHCID 16167369Propylphosphoric anhydrideHCID 593623307-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxylic acid

Product 1

HCID 52932182N-[4-(Aminosulfonyl)-2-methylphenyl]-7-methoxy-2-oxo-8-propyl-2H-chromene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Intermediate 1 (0.10 g, 0.381 mmol) in CH2Cl2 (5.0 mL) was added diisopropyl ethyl amine (0.1 mL, 0.572 mmol) and a 50% solution of propylphosphonic anhydride in ethyl acetate (0.340 mL, 0.572 mmol). The mixture was stirred for 30 minutes at room temperature. 4-Amino-3-methylbenzenesulfonamide [CAS # 53297-70-4] (0.071 g, 0.381 mmol) was added to the reaction mixture at room temperature and stirred overnight. The reaction mixture was then poured onto ice water (25 mL) and CH2Cl2 (25 mL) added. The organic layer was separated and washed with brine (25 mL), dried with Na2SO4, filtered and concentrated to dryness. The residue was triturated with CH2Cl2/Hexanes and then the solid was purified with a MPLC to give the title compound as a white solid.

Workup

  1. stirringstirred overnight
  2. additionadded
  3. customThe organic layer was separated
  4. washwashed with brine (25 mL)
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was triturated with CH2Cl2/Hexanes
  9. customthe solid was purified with a MPLC

Sources & evidence

ORD record
ord-946c9e10ea954933a1f2af04e922051f
Source dataset
uspto-grants-2015_07
Patent number
US09073888B2

Reaction notes

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