Hydrochloric Acid → HCID 57990804, compound

HRID 2091973Notes

Reaction equation

HRID 2091973 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][CH:21]=4)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:30][C:31]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:32]=1[CH:33]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>CN(C=O)C>[Cl:30][C:31]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:32]=1[CH2:33][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[C:18]([C:20]4[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][CH:21]=4)[CH:17]=[CH:16][N:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 134042,4-DichlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57990921HCID 57990921, compound

Product 1

HCID 57990804HCID 57990804, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 1 ml vial was added N-(4-{2-[(4-piperazin-1-ylphenyl)amino]pyrimidin-4-yl}-phenyl)acetamide (38.85 mg, 0.1 mmol), 2,4-dichlorobenzaldehyde (350 mg, 2.0 mmol, 20 eq, source: Aldrich) and 1 ml of DMF. To this mixture was added sodium triacetoxyborohydride (106 mg, 0.5 mmol, 5 eq). The mixture was stirred over night at room temperature. Upon completion of the reaction as determined by LC/MS, 0.1 ml of 2M HCl was added. The residue was purified via reverse phase HPLC (ammonium acetate/ACN) to yield N-(4-{2-[(4-{4-[(2,4-dichlorophenyl)methyl]piperazin-1-yl}phenyl)amino]pyrimidin-4-yl}phenyl)acetamide 180 (20.2 mg, 37%).

Workup

  1. customUpon completion of the reaction
  2. additionwas added
  3. customThe residue was purified via reverse phase HPLC (ammonium acetate/ACN)

Sources & evidence

ORD record
ord-093bcdb4aaca44afa77c268d7ee2bd61
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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