Dichloromethane → HCID 22348277, compound

HRID 897252Notes

Reaction equation

HRID 897252 reaction equation
Cl.CO[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9](=[O:14])[CH:8]=[C:7]2[NH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(Cl)Cl>CO>[NH:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:7]2[C:6]3[C:11](=[CH:12][CH:13]=[CH:4][CH:5]=3)[O:10][C:9](=[O:14])[CH:8]=2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 22348292HCID 22348292, compound

Product 1

HCID 22348277HCID 22348277, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a 4 mL screw cap vial charged with MP-BH3CN resin (Argonaut Technologies, loading 2.32 mmol/g; 0.056 g; 2 eq.) and 6-methoxy-4-(piperidin-4-ylamino)-chromen-2-one hydrochloride (I)(0.020 g, 0.064 mmol) a solution of the corresponding aldehyde (1.5 eq.) in 1.0 mL of 1:1 MeOH:CH2Cl2(1% AcOH) was added. The resulting mixture was agitated at 60° C. for 12 h. Then, additional MP-BH3CN resin (0.028 g; 1 eq.) was added followed by a solution of the aldehyde (0.75 eq.) in 0.5 mL of the same solvent. The resulting mixture was shaken at 60° C. for additional 12 h. The reaction mixture was then filtered and the resin washed with MeOH (1 mL, twice). The filtrate and the washes were combined, evaporated in vacuo and the residual oil was purified by reverse phase HPLC (TFA method).

Workup

  1. customTo a 4 mL screw cap vial
  2. additionThen, additional MP-BH3CN resin (0.028 g; 1 eq.) was added
  3. stirringThe resulting mixture was shaken at 60° C. for additional 12 h
  4. filtrationThe reaction mixture was then filtered
  5. washthe resin washed with MeOH (1 mL
  6. customevaporated in vacuo
  7. customthe residual oil was purified by reverse phase HPLC (TFA method)

Sources & evidence

ORD record
ord-0e4fd1c1a17d4240b16361b746272910
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

Loading…