Dimethylformamide → HCID 66777824, compound

HRID 2091423Notes

Reaction equation

HRID 2091423 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([CH:14]([NH:18][C:19]4[CH:20]=[CH:21][C:22](C(O)=O)=[N:23][CH:24]=4)[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:28])[C:10]=3[CH:29]=2)[CH2:3][CH2:2]1.CNC[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl-].[NH4+].[CH3:63][N:64]([CH3:67])[CH:65]=[O:66]>C(N(CC)CC)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([CH:14]([NH:18][C:19]4[CH:20]=[CH:21][C:22]([C:65]([N:64]([CH3:67])[CH2:63][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:66])=[N:23][CH:24]=4)[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:28])[C:10]=3[CH:29]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66777998HCID 66777998, compound

Product 1

HCID 66777824HCID 66777824, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5-({1-[5-(cyclopropylmethoxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)pyridine-2-carboxylic acid (311 mg) synthesized above, ethyl 3-(methylamino)propanoate (131 mg), 1-hydroxybenzotriazole.monohydrate (145 mg), triethylamine (265 μL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (182 mg) and N,N-dimethylformamide (2 mL) was stirred at room temperature for 16 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-0:100, v/v) to give the title compound (291 mg, 73%) as a colorless amorphous form.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-0:100, v/v)

Sources & evidence

ORD record
ord-d9e9c134c385424bb09d7c244c70d713
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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