Sodium triacetoxyborohydride → HCID 86760444, compound

HRID 456601Notes

Reaction equation

HRID 456601 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15].[C:22]([O:25][BH-](O[C:32](=[O:34])[CH3:33])OC(=O)C)(=[O:24])C.[Na+].[CH3:36][OH:37].C(O[CH2:42][CH3:43])(=O)C>C(Cl)(Cl)Cl.CO>[C:22]([OH:25])(=[O:24])[C:36]([OH:2])=[O:37].[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14]([CH:16]1[CH2:21][CH2:20][N:19]([CH2:16][CH2:14][N:13]2[CH2:6][CH2:5][CH2:10][C:11]3[CH:12]=[CH:3][CH:42]=[CH:43][C:33]=3[C:32]2=[O:34])[CH2:18][CH2:17]1)=[O:15]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11231497Piperidine-4-carboxylic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amideHCID 21584119Ethylacetate methanol

Product 1

HCID 86760444HCID 86760444, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

A solution of amine (1f) (115 mg, 0.4 mmol), aldehyde (b) (90 mg, 0.44 mmol) in chloroform/methanol (2.3 ml/0.3 ml) was treated with freshly activated 3 Å molecular sieves and heated to reflux under argon for 8 hours. The cooled mixture was treated with sodium triacetoxyborohydride (130 mg, 0.6 mmol) and stirred for 16 hours at room temperature. The mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried and evaporated to give a brown oil. Chromatography on silica eluting with a methanol/ethyl acetate gradient afforded the free base of the title compound as an oil (60 mg, 32%).

Workup

  1. temperatureheated
  2. temperatureto reflux under argon for 8 hours
  3. customThe mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. extractionThe organic extract
  5. customwas dried
  6. customevaporated
  7. customto give a brown oil

Sources & evidence

ORD record
ord-e841d18bcf9f4107b4a2dc6e45d5ca38
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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