Benzamidine → HCID 178422219, compound

HRID 1990915Notes

Reaction equation

HRID 1990915 reaction equation
C[O:2][C:3](=O)[CH:4]([C:12]#[N:13])[CH2:5][C:6]1([CH3:11])[O:10][CH2:9][CH2:8][O:7]1.[C:15]([NH2:23])(=[NH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C.C(Cl)(Cl)Cl>[NH2:13][C:12]1[N:23]=[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:22]=[C:3]([OH:2])[C:4]=1[CH2:5][C:6]1([CH3:11])[O:7][CH2:8][CH2:9][O:10]1

Participants

6

Reactant 3

HCID 2332BenzamidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68566357HCID 68566357, compound

Product 1

HCID 178422219HCID 178422219, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of acetal (2) (1 g, 5.02 mmol), benzamidine (786 mg, 5.02 mmol), and DBU (1.5 mL, 10.04 mmol) in dry DMF (15 mL) was heated to 85° C. for 15 h. The mixture was diluted with CHCl3 (30 mL) and washed with 0.5 N NaOH (10 mL) and H2O (20 mL). The organic fraction was dried, filtered and concentrated to a brown oil. Flash chromatography (SiO2; 1/9 EtOAc/CH2Cl2, Rf 0.35) was attempted, but material crystallized on the column. The silica gel was washed with MeOH. Fractions containing the product (3) were concentrated and used without further purification (783 mg, 54.3%):

Workup

  1. washwashed with 0.5 N NaOH (10 mL) and H2O (20 mL)
  2. customThe organic fraction was dried
  3. filtrationfiltered
  4. concentrationconcentrated to a brown oil
  5. custommaterial crystallized on the column
  6. washThe silica gel was washed with MeOH
  7. additionFractions containing the product (3)
  8. concentrationwere concentrated
  9. customused without further purification (783 mg, 54.3%)

Sources & evidence

ORD record
ord-3f8a2c811c52414c8bf71fd582ee64ca
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

Loading…