Acetic Acid → HCID 178473893, compound

HRID 1984628

Reaction equation

HRID 1984628 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[CH:12][C:13]3[CH:19]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:17]([C:26]4[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=4)=[N:16][C:14]=3[N:15]=2)[CH2:6][CH2:5]1)(=O)C.F[C:35](F)(F)[C:36]([OH:38])=O.[NH:41]1[CH2:46][CH2:45][CH:44]([C:47]2[NH:48][C:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=3)=[N:50][N:51]=2)[CH2:43][CH2:42]1.CCN(CC)CC.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.CCOC(C)=O>[C:36]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:11]=[CH:12][C:13]3[CH:19]=[C:18]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:17]([C:26]4[CH:33]=[CH:32][C:29]([CH2:30][N:41]5[CH2:46][CH2:45][CH:44]([C:47]6[NH:48][C:49]([C:52]7[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=7)=[N:50][N:51]=6)[CH2:43][CH2:42]5)=[CH:28][CH:27]=4)=[N:16][C:14]=3[N:15]=2)[CH2:8][CH2:9]1)(=[O:38])[CH3:35]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 577139444-[2-(4-Acetylpiperazin-1-yl)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]benzaldehydeHCID 178525658HCID 178525658, compound

Product 1

HCID 178473893HCID 178473893, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[2-(4-acetylpiperazin-1-yl)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]benzaldehyde (3-2; 61 mg, 0.14 mmol) in DMF (5 mL) was added 2-(5-piperidin-4-yl-4H-1,2,4-triazol-3-yl)pyridine trifluoroacetate (58 mg, 0.17 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 residue was purified by silica gel chromatography (100% CH2Cl2 to 85% CH2Cl2/15% MeOH) to afford the title compound. LRMS m/z (M+H) Calcd.: 651.7, found 651.3.

Workup

  1. washwashed with NaHCO3 (sat.)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (100% CH2Cl2 to 85% CH2Cl2/15% MeOH)

Sources & evidence

ORD record
ord-8682c367792c4693b4d39c1d3acfd771
Source dataset
uspto-grants-2009_06
Patent number
US07544677B2

Linked notes

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