Sodium triacetoxyborohydride → HCID 68819065, compound

HRID 657126Notes

Reaction equation

HRID 657126 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[C:13]([O:21][CH3:22])=[CH:12][C:11]2=[O:23])[CH2:4][CH2:3]1.[O:24]1[C:33]2[CH:32]=[C:31]([CH:34]=O)[N:30]=[CH:29][C:28]=2[O:27][CH2:26][CH2:25]1.[Cl:36]CCl.CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[ClH:36].[ClH:36].[O:24]1[C:33]2[CH:32]=[C:31]([CH2:34][NH:1][CH:2]3[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]4[C:19]5[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=5)[C:13]([O:21][CH3:22])=[CH:12][C:11]4=[O:23])[CH2:6][CH2:7]3)[N:30]=[CH:29][C:28]=2[O:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 5049666Sodium triacetoxyborohydrideHCID 21226129Dichloromethane methanolHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 68816900HCID 68816900, compound

Product 1

HCID 68819065HCID 68819065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-4-(methyloxy)-2(1H)-quinolinone (0.057 g, 0.18 mmol) and 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (for a synthesis see WO2004058144, Example 2(c) or WO03/087098, Example 19(d)) (0.027 g, 0.16 mmol) in 1:1 dichloromethane/methanol (4 ml) was stirred with 3A sieves for 2 h then sodium triacetoxyborohydride (0.115 g, 0.54 mmol) added and the mixture stirred overnight. The solution was diluted with dichloromethane and washed with sodium carbonate solution. The aqueous was extracted with dichloromethane/methanol (10%) and the combined organics dried and concentrated. Chromatography over silica (20 g SPE gradient elution dichloromethane/methanol 0-20%) provided the free base of the title compound (0.022 g) which was converted to the title dihydrochloride salt by dissolving in dichloromethane and adding 4N HCl in 1,4-dioxane. Ether was added to the solution and the precipitate collected (0.022 g, 23%).

Workup

  1. washwashed with sodium carbonate solution
  2. extractionThe aqueous was extracted with dichloromethane/methanol (10%)
  3. customthe combined organics dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e97a7f773ee2464286a2ac60b0c7d815
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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