Hydrochloric Acid → HCID 11422109, compound

HRID 2373675Notes

Reaction equation

HRID 2373675 reaction equation
[CH3:1][S:2][C:3]1[C:8]([NH:9][C:10](=[O:21])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19]O)[CH2:14][CH2:13]2)=[C:7]([S:22][CH3:23])[CH:6]=[C:5]([CH3:24])[N:4]=1.[CH2:25]([O:32][C:33]1[CH:42]=[CH:41][C:36]2[N:37]=[C:38]([SH:40])[NH:39][C:35]=2[CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.Cl>CN(C)C=O.C(OCC)(=O)C>[CH2:25]([O:32][C:33]1[CH:42]=[CH:41][C:36]2[N:37]=[C:38]([S:40][CH2:19][CH2:18][N:15]3[CH2:16][CH2:17][N:12]([CH2:11][C:10]([NH:9][C:8]4[C:3]([S:2][CH3:1])=[N:4][C:5]([CH3:24])=[CH:6][C:7]=4[S:22][CH3:23])=[O:21])[CH2:13][CH2:14]3)[NH:39][C:35]=2[CH:34]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 116892402-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]acetamideHCID 178527803HCID 178527803, compound

Product 1

HCID 11422109HCID 11422109, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide (1.00 g, 2.70 mmol), 5-benzyloxy-2-mercaptobenzimidazole (2.57 g, 10.0 mmol), and triphenylphosphine (2.50 g, 9.53 mmol) were dissolved in N,N-dimethylformamide (30 mL). To the solution, under cooling with ice, diethyl azodicarboxylate (1.27 mL, 8.07 mmol) was added dropwise, followed by stirring for one hour at the same temperature. Ethyl acetate and 1 mol/L hydrochloric acid were added to the reaction mixture. The aqueous layer was separated from the mixture, and the organic layer was further extracted with 1 mol/L hydrochloric acid. The obtained aqueous layers were combined and adjusted to basic conditions with a 1 mol/L aqueous sodium hydroxide solution, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, followed by drying over sodium sulfate anhydrate. The solvent was removed under reduced pressure. The thus-obtained residue was purified through silica gel column chromatography (chloroform : saturated ammonia-methanol=20:1), to thereby yield 1.56 g of 2-[4-[2-(5-benzyloxybenzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]acetamide as a colorless amorphous product (yield 94.9%).

Workup

  1. additionwas added dropwise
  2. customThe aqueous layer was separated from the mixture
  3. extractionthe organic layer was further extracted with 1 mol/L hydrochloric acid
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was sequentially washed with water and saturated brine
  6. dry with materialby drying over sodium sulfate anhydrate
  7. customThe solvent was removed under reduced pressure
  8. customThe thus-obtained residue was purified through silica gel column chromatography (chloroform : saturated ammonia-methanol=20:1)

Sources & evidence

ORD record
ord-1273b379d16040ab8106f62fed88b6eb
Source dataset
uspto-grants-2008_12
Patent number
US07459552B2

Reaction notes

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