Diisopropylethylamine → HCID 66990394, compound

HRID 2407680Notes

Reaction equation

HRID 2407680 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]([OH:14])=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[Cl:54][C:55]1[CH:70]=[CH:69][C:58]([C:59]([NH:61][CH2:62][CH:63]2[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]2)=[O:60])=[CH:57][C:56]=1[O:71][CH3:72]>ClCCl>[Cl:54][C:55]1[CH:70]=[CH:69][C:58]([C:59]([NH:61][CH2:62][CH:63]2[CH2:64][CH2:65][N:66]([C:12]([C:10]3[O:9][N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:11]=3)=[O:14])[CH2:67][CH2:68]2)=[O:60])=[CH:57][C:56]=1[O:71][CH3:72]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 7374743-Phenylisoxazole-5-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66989233HCID 66989233, compound

Product 1

HCID 66990394HCID 66990394, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-phenylisoxazole-5-carboxylic acid (0.075 g) in dichloromethane (1.6 mL) was treated with 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.084 g), 1-hyroxybenzotriazole hydrate (0.067 g) and diisopropylethylamine (0.21 mL) and stirred for five minutes. The product prepared in Example 11 (0.17 g) was added and the mixture was stirred at room temperature overnight. The mixture was partitioned between 1 N hydrochloric acid and dichloromethane. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=9:1) to obtain the title compound (0.077 g) having the following physical data.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe mixture was partitioned between 1 N hydrochloric acid and dichloromethane
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-296dd73c92184b2584cc7091926a3b51
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…