Dimethylformamide → HCID 66777839, compound

HRID 2091420Notes

Reaction equation

HRID 2091420 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[N:24]=[CH:23][C:22](C(O)=O)=[CH:21][CH:20]=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[N:24]=[CH:23][C:22]([C:65]([N:64]([CH3:67])[CH2:63][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:66])=[CH:21][CH:20]=4)[CH:15]([CH3:16])[CH3:17])=[C:11]([CH3:28])[C:10]=3[CH:29]=2)[CH2:2][CH2:3]1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66778587HCID 66778587, compound

Product 1

HCID 66777839HCID 66777839, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 6-({1-[5-(cyclopropylmethoxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropyl}amino)pyridine-3-carboxylic acid (145 mg) synthesized above, ethyl 3-(methylamino)propanoate (58 mg), 1-hydroxybenzotriazole.monohydrate (67 mg), triethylamine (122 μL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (84 mg) and N,N-dimethylformamide (2 mL) was stirred at room temperature for 18 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 (104 mg, 56%) 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-5913ee7375e446249c8e89fe5b80df7e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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