Benzaldehyde → HCID 58168037, compound

HRID 1029256Notes

Reaction equation

HRID 1029256 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:17]=[CH:16][N:15]=[C:14]3[C:9]=2[C:10]2[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=2[C:12](=[O:18])[NH:13]3)[CH2:3][CH2:2]1.[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:23]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]2[CH:17]=[CH:16][N:15]=[C:14]3[C:9]=2[C:10]2[CH:22]=[CH:21][CH:20]=[CH:19][C:11]=2[C:12](=[O:18])[NH:13]3)[CH2:5][CH2:6]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 581681941-(4-Piperidinylamino)benzo[c][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58168037HCID 58168037, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

358 (60 mg, 0.20 mmol) and benzaldehyde (0.03 mL, 0.26 mmol) were suspended in DCE (4 mL), and stirred for 2 h at room temperature. NaBH(OAc)3 (130 mg, 0.61 mmol) was added, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with 1NHCl and the crude material was purified directly via HPLC to provide 361 (22 mg, 28% yield) as a solid. LC-MS (M+H=385, obsd.=385).

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. customThe reaction mixture was quenched with 1NHCl and the crude material
  3. customwas purified directly via HPLC

Sources & evidence

ORD record
ord-4e782672069b48639edb2f27fe45895c
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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