Acetic Acid → HCID 178442441, compound

HRID 425389Notes

Reaction equation

HRID 425389 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[CH3:5][C:6]([CH3:29])([CH2:27][CH3:28])[CH2:7][C:8]1[N:9]=[C:10]([CH:13]([NH2:26])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[N:23][NH:24][CH:25]=3)=[CH:17][CH:16]=2)[NH:11][CH:12]=1.Cl.CN(C)CCCN=C=N[CH2:39][CH3:40].[OH:42]N1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CN(C)C=O.O>[C:39]([N:24]1[CH:25]=[C:21]([C:18]2[CH:17]=[CH:16][C:15]([CH2:14][CH:13]([NH:26][C:1](=[O:4])[CH3:2])[C:10]3[NH:11][CH:12]=[C:8]([CH2:7][C:6]([CH3:29])([CH3:5])[CH2:27][CH3:28])[N:9]=3)=[CH:20][CH:19]=2)[CH:22]=[N:23]1)(=[O:42])[CH3:40]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178442463HCID 178442463, compound

Product 1

HCID 178442441HCID 178442441, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic acid (8 mL, 0.014 mmol) was added to an ambient temperature solution of 1-[4-(2,2-dimethyl-butyl)-1H-imidazol-2-yl]-2-[4-(1H-pyrazol-4-yl)phenyl]ethanamine (Example 37) (23 mg, 0.007 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (26 mg, 0.014 mmol), 1-hydroxybenzotriazole (18 mg, 0.014 mmol) and sodium bicarbonate (57 mg, 0.07 mmol) in methylene chloride (5 mL) and N,N-dimethylformamide (0.5 mL). After stirring at ambient temperature overnight, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-25% methanol/ethyl acetate afforded the title compound. (M+H) found: 422.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-415aa4a666054429a1636caa835a6d9a
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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