1,2-Dichloroethane → HCID 58537173, compound

HRID 1804495Notes

Reaction equation

HRID 1804495 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]=1[C:16]([OH:18])=O)=[O:4].Cl.CN.C1C=CC2N(O)N=[N:28][C:26]=2C=1.C(Cl)CCl.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:26][NH:28][C:16]([C:6]1[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][O:9][C:5]=1[C:3]([O:2][CH3:1])=[O:4])=[O:18]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 58537213HCID 58537213, compound

Product 1

HCID 58537173HCID 58537173, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(methoxycarbonyl)-3-phenylisoxazole-4-carboxylic acid (50 mg, 0.202 mmol), methylamine hydrochloride (19.12 mg, 0.283 mmol), HOBT (37.2 mg, 0.243 mmol), EDC (46.5 mg, 0.243 mmol) and diisopropylethylamine (0.141 mL, 0.809 mmol) in DMF was stirred at rt for 22 hr. The reaction mixture was partitioned between EtOAc (30 mL) and water (30 mL). The organic layer was washed with saturated potassium bisulfate solution (30 ml), saturated sodium bicarbonate solution (30 mL) and brine (30 mL). After drying (MgSO4) and filtration, the organic layer was concentrated to afford methyl 4-(methylcarbamoyl)-3-phenylisoxazole-5-carboxylate (38 mg, 0.146 mmol, 72.2% yield) as a tan solid. HPLC retention time=1.09 minutes (YMC Combi 4.6×30 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.1 TFA a 2 minute gradient. MS: (M+H)=261.15. 1H NMR (400 MHz, chloroform-d) d ppm 2.97 (d, J=4.77 Hz, 3H) 4.04 (s, 3 H) 7.19 (brs, 1H) 7.42-7.51 (m, 3H) 7.66-7.73 (m, 2H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc (30 mL) and water (30 mL)
  2. washThe organic layer was washed with saturated potassium bisulfate solution (30 ml), saturated sodium bicarbonate solution (30 mL) and brine (30 mL)
  3. customAfter drying
  4. filtration(MgSO4) and filtration
  5. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-023664cec5d244e8b3f070f844534104
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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