Acetic Acid → HCID 66965860, compound

HRID 1514852Notes

Reaction equation

HRID 1514852 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.CCN(C(C)C)C(C)C.[C:28](O)(=[O:30])[CH3:29].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>O1CCOCC1.CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([NH:18][C:28](=[O:30])[CH3:29])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 28370697HCID 28370697, compound

Product 1

HCID 66965860HCID 66965860, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a vial containing a solution of 2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-ylamine in dioxane (0.2 M, 0.10 mL) was added DIPEA (0.5 M in toluene, 0.050 mL) and acetic acid (0.2 M in toluene, 0.12 mL), followed by BOP reagent (0.2 M in DMF, 0.15 mL). After overnight at ambient temperature, the mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to N-[2-(2-Chloro-phenyl)-3H-benzoimidazol-5-yl]-acetamide: MS (m/z) 320.02 (M+1).

Workup

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography to N-[2-(2-Chloro-phenyl)-3H-benzoimidazol-5-yl]-acetamide

Sources & evidence

ORD record
ord-9b4ba0258fa04eb499af6a1425f45fa2
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…