HCID 3078154, compound → HCID 21073225, compound

HRID 1373627Notes

Reaction equation

HRID 1373627 reaction equation
[CH3:1][C:2]1[C:3]2[CH:17]=[CH:16][C:15](=[O:18])[NH:14][C:4]=2[N:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][CH:12]=O)[N:7]=1.[CH:19]([C:22]1[N:27]=[C:26]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:24][CH:23]=1)([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:19]([C:22]1[N:27]=[C:26]([N:28]2[CH2:33][CH2:32][N:31]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:6]3[N:7]=[C:2]([CH3:1])[C:3]4[CH:17]=[CH:16][C:15](=[O:18])[NH:14][C:4]=4[N:5]=3)[CH2:30][CH2:29]2)[CH:25]=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 3078154HCID 3078154, compoundHCID 5049666Sodium triacetoxyborohydrideHCID 21073351HCID 21073351, compound

Product 1

HCID 21073225HCID 21073225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-yloxy)-butyraldehyde (74.2 mg, 0.3 mmol) and 1-(6-isopropyl-pyridin-2-yl)-piperazine (62.8 mg, 0.306 mmol) were combined in methylene chloride and stirred in a vial over sieves for 10 min. Sodium triacetoxyborohydride (89 mg, 0.42 mmol) was added and the reaction was stirred overnight. The reaction was quenched by slowly adding water and then the mixture was filtered. The residue was partitioned between CH2Cl2 and water and the organic layer was concentrated. Purification by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% of a 10% MeOH in CH2Cl2 solution) gave the title compound as a low melting solid (55 mg, 0.126 mmol, 42%). MS: APCI: M+1: 437.3 (Exact Mass: 436.26).

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe reaction was quenched by slowly adding water
  3. filtrationthe mixture was filtered
  4. customThe residue was partitioned between CH2Cl2 and water
  5. concentrationthe organic layer was concentrated
  6. customPurification by liquid chromatography (MPLC, gradient of 100% CH2Cl2 to 100% of a 10% MeOH in CH2Cl2 solution)

Sources & evidence

ORD record
ord-ffffcf562cd942dfa1c56edae303d6fc
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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