Acetic Acid → HCID 178488200, compound

HRID 432323Notes

Reaction equation

HRID 432323 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:23][CH2:22][C@H:21]([N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[N:9]=2)=[CH:4][CH:3]=1.[C:31]([O:34][BH-]([O:40][C:41](=[O:43])[CH3:42])OC(=O)C)(=[O:33])[CH3:32].[Na+].[C:45]([OH:48])(=[O:47])[CH3:46]>ClCCCl>[C:41]([OH:40])(=[O:43])/[CH:42]=[CH:46]\[C:45]([OH:48])=[O:47].[C:31]([OH:34])(=[O:33])/[CH:32]=[CH:46]\[C:45]([OH:48])=[O:47].[CH3:45][O:48][C:7]1[CH:6]=[C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@H:18]3[CH2:23][CH2:22][C@H:21]([N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH2:20][CH2:19]3)[N:9]=2)[CH:4]=[CH:3][C:2]=1[NH:1][CH2:4][C:3]1[O:43][C:41]([CH3:42])=[CH:7][CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 178480984HCID 178480984, compound

Product 1

HCID 178488200HCID 178488200, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of the cis-or trans-3-(4-amino-phenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (either intermediate . . . or . . . ) (1 eq.), aldehyde (1 eq.), sodium triacetoxyborohydride (3.4 eq.) and acetic acid (3.4 eq) was stirred in anhydrous 1,2-dichloroethane for 16 hours. The reaction mixture was concentrated under reduced pressure, quenched with saturated solution of sodium bicarbonate in water and concentrated again. The residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield the desired products.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customquenched with saturated solution of sodium bicarbonate in water
  3. concentrationconcentrated again
  4. customThe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-2ae42611bead4a9faa7dc0ba0242ba81
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

Loading…