Dimethylformamide → HCID 178496104, compound

HRID 491787Notes

Reaction equation

HRID 491787 reaction equation
Cl.Cl.[CH3:3][O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=3)=[O:17])=[C:13]([NH:26][C:27]([C@H:29]3[CH2:34][CH2:33][C@H](NC)[CH2:31][CH2:30]3)=[O:28])[C:12]=2[CH:37]=1.ON1C2C=CC=C[C:42]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+].[CH3:65][N:66]([CH3:69])[CH:67]=[O:68]>C(N(CC)CC)C.C(O)(=O)C>[C:67]([N:66]([C@H:69]1[CH2:33][CH2:34][C@H:29]([C:27]([NH:26][C:13]2[C:12]3[CH:37]=[C:8]([O:7][CH2:6][CH2:5][O:4][CH3:3])[CH:9]=[CH:10][C:11]=3[O:15][C:14]=2[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][N:20]=2)=[O:17])=[O:28])[CH2:30][CH2:31]1)[CH3:65])(=[O:68])[CH3:42]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 757711-Hydroxybenzotriazole2×HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 178484812HCID 178484812, compound

Product 1

HCID 178496104HCID 178496104, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

Trans-5-(2-methoxyethoxy)-3-[4-(methylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide dihydrochloride (110 mg) obtained in Example 223 is suspended in N,N-dimethylformamide (5 ml), and thereto are added successively acetic acid (13.2 μl), 1-hydroxybenzotriazole (31 mg), triethylamine (80 μl) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (44 mg), and the mixture is stirred at room temperature for 15 hours. To the reaction solution are added acetic acid (8.2 μl), 1-hydroxybenzotriazole (20 mg), triethylamine (67 μl) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (28 mg), and the mixture is further stirred at room temperature for 20 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is washed with a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then ethyl acetate). The obtained solid is suspended in n-hexane/diisopropyl ether, and collected by filtration to give the title compound (42 mg).

Workup

  1. stirringthe mixture is further stirred at room temperature for 20 hours
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe resulting residue is purified by NH-silica gel column chromatography (eluent
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-af6f0834e4e44dc4bbf49bd1057b6e89
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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