Sodium triacetoxyborohydride → HCID 178430598, compound

HRID 1963967Notes

Reaction equation

HRID 1963967 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][CH2:23][C:24]4(C)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[N:16]=3)[C:12]([Cl:31])=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[CH3:32][C:33]1([CH:38]=O)[O:37][CH2:36][CH2:35][O:34]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.O>[Cl:31][C:12]1[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([NH:22][CH2:23][CH:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[N:16]=2)=[CH:14][C:9]([NH:8][C@H:5]2[CH2:6][CH2:7][C@H:2]([NH:1][CH2:32][C:33]3([CH3:38])[O:37][CH2:36][CH2:35][O:34]3)[CH2:3][CH2:4]2)=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 110188392-methyl-1,3-dioxolane-2-carbaldehydeHCID 178430098HCID 178430098, compound

Product 1

HCID 178430598HCID 178430598, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N2′-(trans-4-aminocyclohexyl)-5′-chloro-5-fluoro-N6-((4-methyltetrahydro-2H-pyran-4-yl)methyl)-2,4′-bipyridine-2′,6-diamine (21 mg, 0.048 mmol) in DCM (1.0 ml) was added 2-methyl-1,3-dioxolane-2-carbaldehyde (synthesized following the procedure reported in Org. Lett., 2009,11, 3542-3545), sodium triacetoxyborohydride (20.51 mg, 0.097 mmol). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed sequentially with water and brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by reverse phase HPLC and lyophilized to give 12 mg off-white powder of the title compound as its TFA salt. LCMS (m/z): 534.1 (MH+), retention time=0.62 min.

Workup

  1. customsynthesized
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed sequentially with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-5cbcd42318f842d599d5e69d93f845d6
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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