Diisopropylethylamine → 4-nitrophenyl 7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate

HRID 528584Notes

Reaction equation

HRID 528584 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Cl[C:39]([O:41][C:42]1[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=1)=[O:40]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:39]([O:41][C:42]4[CH:43]=[CH:44][C:45]([N+:48]([O-:50])=[O:49])=[CH:46][CH:47]=4)=[O:40])[CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformate2×HCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide2×

Product 1

HCID 897616924-nitrophenyl 7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (INTERMEDIATE M, 0.200 g, 0.479 mmol) and Hunig's base (0.092 ml, 0.527 mmol) in DCM (2.395 ml) was added 4-nitrophenyl chloroformate (0.097 g, 0.479 mmol) (change from colorless to light yellow solution). The reaction was stirred at RT overnight, at which point starting material remained. Additional 4-nitrophenyl chloroformate (0.097 g, 0.479 mmol) was added and the reaction was stirred overnight once more until completion. After concentration in vacuo, the material was purified via MPLC (12-g Redi Sep Gold) eluting with 0-100% ethyl acetate in heptanes, to yield 4-nitrophenyl 7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazine-4(3H)-carboxylate as a white solid. m/z (ESI) 583.0 (M+H)+.

Workup

  1. stirringthe reaction was stirred overnight once more until completion
  2. concentrationAfter concentration in vacuo
  3. customthe material was purified via MPLC (12-g Redi Sep Gold)
  4. washeluting with 0-100% ethyl acetate in heptanes

Sources & evidence

ORD record
ord-93557e8418c7411d8a2f0fe6937bd774
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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