Formaldehyde → HCID 54765084, compound

HRID 85069Notes

Reaction equation

HRID 85069 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([C:19]5[CH:24]=[CH:23][C:22]([CH2:25][N:26]6[CH2:31][CH2:30][NH:29][CH:28]([CH3:32])[CH2:27]6)=[CH:21][CH:20]=5)[CH:17]=4)[N:12](S(C4C=CC(C)=CC=4)(=O)=O)[CH:11]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH2:43]1COCC1.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:32][CH:28]1[N:29]([CH3:43])[CH2:30][CH2:31][N:26]([CH2:25][C:22]2[CH:23]=[CH:24][C:19]([C:16]3[CH:17]=[C:18]4[C:10]([C:6]5[CH:5]=[C:4]6[C:9](=[CH:8][CH:7]=5)[NH:1][CH:2]=[CH:3]6)=[CH:11][NH:12][C:13]4=[N:14][CH:15]=3)=[CH:20][CH:21]=2)[CH2:27]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 70648378HCID 70648378, compound

Product 1

HCID 54765084HCID 54765084, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(1H-indol-5-yl)-5-(4-((3-methylpiperazin-1-yl)methyl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (40 mg) was suspended in 3 mL of methanol and THF (1 mL) and treated with paraformaldehyde (−50 mg) and stirred for one hour. To this was added 50 mg of sodium triacetoxyborohydride. The reaction stirred 1 hr at room temperature. The mixture was concentrated in vacuo, taken up in EtOAc and washed with water and brine and dried over MgSO4. The residue was suspended in methanol and treated with 5 N NaOH and heated at 50 C for one hour. The mixture was diluted with dichloromethane and washed with water and brine, dried over MgSO4 and purified by MPLC silica gel chromatography (0-20% MeOH in DCM) to yield an analytical sample 10 mg (436 M+H).

Workup

  1. stirringThe reaction stirred 1 hr at room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. additiontreated with 5 N NaOH
  6. temperatureheated at 50 C for one hour
  7. additionThe mixture was diluted with dichloromethane
  8. washwashed with water and brine
  9. dry with materialdried over MgSO4
  10. custompurified by MPLC silica gel chromatography (0-20% MeOH in DCM)
  11. customto yield an analytical sample 10 mg (436 M+H)

Sources & evidence

ORD record
ord-431288ca568b4788921772d9896ea48a
Source dataset
uspto-grants-2014_09
Patent number
US08846909B2

Reaction notes

Loading…