Diisopropylethylamine → HCID 69652677, compound

HRID 1823286Notes

Reaction equation

HRID 1823286 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:17])[C:7]=1[C:8]1[C:12]([C:13]([OH:15])=O)=[C:11]([CH3:16])[O:10][N:9]=1.[CH2:18]([O:25][C:26](=[O:36])[NH:27][CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH2:35])[CH2:30]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH2:18]([O:25][C:26](=[O:36])[NH:27][CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:13]([C:12]2[C:8]([C:7]3[C:6]([Cl:17])=[CH:5][N:4]=[CH:3][C:2]=3[Cl:1])=[N:9][O:10][C:11]=2[CH3:16])=[O:15])[CH2:30]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22170140HCID 22170140, compoundHCID 22714145(3-Amino-cyclohexylmethyl)-carbamic acid benzyl ester

Product 1

HCID 69652677HCID 69652677, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3-(3,5-dichloro-pyridin-4-yl)-5-methyl-isoxazole-4-carboxylic acid (0.41 g, 0.0015 mol) with (3-amino-cyclohexylmethyl)-carbamic acid benzyl ester (0.45 g, 0.0015 mol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.29, 0.0015 mol), 1-hydroxy-7-azabenzo-triazole (0.20 g, 0.0015 mol), and N,N-diisopropylethyl amine (0.78 mL, 0.0045 mol), in N,N-dimethylformamide (10 mL) and stir over a weekend at ambient temperature. Concentrate the mixture in vacuo and take up in water and extracte with ethyl acetate. Dry over sodium sulfate. Concentrate and elute over silica gel using methanol/dichloromethane to give 0.64 g (82%) of the desired amide as a white foam. MS(ES): (M+1)+ 516.9, 518.9 m/z.

Workup

  1. concentrationConcentrate the mixture in vacuo
  2. dry with materialDry over sodium sulfate
  3. concentrationConcentrate
  4. washelute over silica gel

Sources & evidence

ORD record
ord-e98fe8096bdc4952aca593de7f6b8541
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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