Acetic Acid → HCID 178521486, compound

HRID 1984639Notes

Reaction equation

HRID 1984639 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]3[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:18]([C:27]4[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=4)=[N:17][C:15]=3[N:16]=2)[CH2:7][CH2:6]1)(=[O:4])[CH2:2][OH:3].O=[C:36]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)[CH2:37]O.F[C:46](F)(F)[C:47](O)=O.N1CCC(C2NC(C3C=CC=CN=3)=[N:61][N:62]=2)CC1.[CH3:69][CH2:70][N:71](CC)[CH2:72][CH3:73].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCOC(C)=O>[O:4]=[C:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:12]=[CH:13][C:14]3[CH:20]=[C:19]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:18]([C:27]4[CH:34]=[CH:33][C:30]([CH2:31][N:71]5[CH2:72][CH2:73][CH:37]([C:36]6[NH:39][C:44]([C:43]7[CH:47]=[CH:46][CH:40]=[CH:41][N:42]=7)=[N:62][N:61]=6)[CH2:69][CH2:70]5)=[CH:29][CH:28]=4)=[N:17][C:15]=3[N:16]=2)[CH2:7][CH2:6]1)[CH2:2][OH:3]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 185068842-Hydroxy-1-(piperazin-1-yl)ethan-1-oneHCID 577139604-[2-(4-Glycoloylpiperazin-1-yl)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]benzaldehydeHCID 178525658HCID 178525658, compound

Product 1

HCID 178521486HCID 178521486, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[2-(4-glycoloylpiperazin-1-yl)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]benzaldehyde (8-1) (136 mg, 0.292 mmol, prepared from 6-4 and 2-oxo-2-piperazin-1-ylethanol according to the procedure described for the synthesis of 7-1) in DM (5 mL) was added 2-(5-piperidin-4-yl-4H-1,2,4-triazol-3-yl)pyridine trifluoroacetate (73 mg, 0.32 mmol) followed by Et3N (80 μL, 0.51 mmol), AcOH (91 μL, 1.5 mmol) and sodium triacetoxyborohydride (59 mg, 0.28 mmol). The reaction mixture was allowed to stir for 12 hr then diluted with EtOAc and washed with NaHCO3 (sat.), dried with MgSO4, filtered, and concentrated under reduced pressure. The oily residue was purified by reverse phase HPLC (Acetonitrile/0.1% TFA in water gradient) to afford the title compound. LRMS m/z (M+H) Calcd.: 667.8, found 667.5.

Workup

  1. customdescribed for the synthesis of 7-1) in DM (5 mL)
  2. washwashed with NaHCO3 (sat.)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe oily residue was purified by reverse phase HPLC (Acetonitrile/0.1% TFA in water gradient)

Sources & evidence

ORD record
ord-03655898f2924acf9d9bc50f6257038a
Source dataset
uspto-grants-2009_06
Patent number
US07544677B2

Reaction notes

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