Sodium borohydride → HCID 73213951, compound

HRID 1398379Notes

Reaction equation

HRID 1398379 reaction equation
[C:1]([C:4]1[C:20]([O:21][CH2:22][C@@H:23]([NH2:28])[CH2:24][CH:25]([CH3:27])[CH3:26])=[CH:19][C:7]2[N:8]([CH3:18])[C:9](=[O:17])[C:10]3[C:15]([C:6]=2[CH:5]=1)=[CH:14][CH:13]=[N:12][C:11]=3[CH3:16])(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[NH2:28][C@@H:23]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:22][O:21][C:20]1[C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][C:6]2[C:15]3[C:10](=[C:11]([CH3:16])[N:12]=[CH:13][CH:14]=3)[C:9](=[O:17])[N:8]([CH3:18])[C:7]=2[CH:19]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86710371HCID 86710371, compound

Product 1

HCID 73213951HCID 73213951, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-9-acetyl-8-((2-amino-4-methylpentyl)oxy)-4,6 dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (100 mg, 0.257 mmol) in Ethanol (2 mL) was added NaBH4 (97 mg, 2.57 mmol) at 0° C. The reaction mixture was allowed to stir at RT for 16 h. Then, it was quenched with NH4Cl, diluted with water and extracted in ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated. The crude reaction mixture was purified by prep. HPLC which afforded 8-(((S)-2-amino-4-methylpentyl)oxy)-9-(1-hydroxyethyl)-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (0.03 g, 27% yield) as pale yellow semi-solid. LC/MS (ESI) m/e 384.1 [(M+H)+, calcd for C22H30N3O3, 384.2]; LC/MS retention time (method E): tR=0.73 min.

Workup

  1. customThen, it was quenched with NH4Cl
  2. additiondiluted with water
  3. extractionextracted in ethyl acetate
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude reaction mixture
  7. customwas purified by prep

Sources & evidence

ORD record
ord-6bedf72a5e714145af214ee828545f1a
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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