Diisopropylethylamine → HCID 69652682, compound

HRID 1823300Notes

Reaction equation

HRID 1823300 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[C:13]([C:14]([OH:16])=O)=[C:12]([CH3:17])[O:11][N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=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:14]([C:13]2[C:9]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=3)=[N:10][O:11][C:12]=2[CH3:17])=[O:16])[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 22170145HCID 22170145, compoundHCID 22714145(3-Amino-cyclohexylmethyl)-carbamic acid benzyl ester

Product 1

HCID 69652682HCID 69652682, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 3-(3,5-dichloro-pyridin-2-yl)-5-methyl-isoxazole-4-carboxylic acid (0.35 g, 0.0013 mol) with (3-amino-cyclohexylmethyl)-carbamic acid benzyl ester (0.38 g, 0.0013 mol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.25, 0.0013 mol), 1-hydroxy-7-azabenzo-triazole (0.18 g, 0.0013 mol), and N,N-diisopropylethyl amine (0.67 mL, 0.0039 mol) in N,N-dimethylformamide (8 mL) and stir overnight at ambient temperature. Concentrate in vacuo and take up in water and extract with dichloromethane. Concentrate and elute over silica gel using ethyl acetate/dichloromethane to give 0.603 g (90%) of the desired amide. MS(ES): (M+1)+ 517.2, 519.2 m/z.

Workup

  1. concentrationConcentrate in vacuo
  2. extractionextract with dichloromethane
  3. concentrationConcentrate
  4. washelute over silica gel

Sources & evidence

ORD record
ord-189a692ae29a4d669cd9b0939e9eb1c6
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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