1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl N-(3-(4-methoxyphenyl)-5-methylisoxazole-4-carbonyl)(methylthio)carbonoimidoylcarbamate

HRID 1432075Notes

Reaction equation

HRID 1432075 reaction equation
[CH3:1][S:2][C:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[NH:4].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:25]([C:26](O)=[O:27])=[C:24]([CH3:29])[O:23][N:22]=2)=[CH:17][CH:16]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[C:25]([C:26]([N:5]([C:3]([S:2][CH3:1])=[NH:4])[C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:27])=[C:24]([CH3:29])[O:23][N:22]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27797643-(4-Methoxyphenyl)-5-methylisoxazole-4-carboxylic acidHCID 137319820tert-butyl N-[(methylsulfanyl)methanimidoyl]carbamate

Product 1

HCID 86609632tert-butyl N-(3-(4-methoxyphenyl)-5-methylisoxazole-4-carbonyl)(methylthio)carbonoimidoylcarbamateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl methylthiocarbonoimidoylcarbamate (Preparation AU, 0.98 g, 5.16 mmol), 3-(4-methoxyphenyl)-5-methyl-4-isoxazolecarboxylic acid (Preparation Y, 1.17 g, 5 mmol), EDCI (1.2 g, 6.26 mmol) and DIPEA (1 g, 7.75 mmol) in DCM (30 mL) was stirred for 3 hours. The solvent was concentrated by rotovap and residue was purified by column with EtOAc/DCM (5/95) as the eluant. The product was obtained as a white solid (1.2 g, 60%). 1H NMR (CD3OD): δ 1.52 (s, 9H), 1.89 (s, 3H), 2.76 (s, 3H), 3.86(s, 3H), 7.00,7.02 (d, 2H), 7.47,7.49 (d, 2H). MH+=406.19

Workup

  1. concentrationThe solvent was concentrated by rotovap and residue
  2. customwas purified by column with EtOAc/DCM (5/95) as the eluant

Sources & evidence

ORD record
ord-3d2fca8c9c974a45a172e3f95be3685d
Source dataset
uspto-grants-2009_11
Patent number
US07612069B2

Reaction notes

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