Sodium borohydride → HCID 66774031, compound

HRID 255385Notes

Reaction equation

HRID 255385 reaction equation
[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]4[C:30]5[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=5)[N:24]=[CH:23][C:22]4=[O:33])[CH2:15][CH2:14]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C>[O:1]1[C:10]2[CH:9]=[C:8]([CH2:11][NH:12][CH:13]3[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][N:21]4[C:30]5[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=5)[NH:24][CH2:23][C:22]4=[O:33])[CH2:17][CH2:18]3)[N:7]=[CH:6][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 159825331-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-7-methoxyquinoxalin-2(1H)-one

Product 1

HCID 66774031HCID 66774031, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-7-methoxyquinoxalin-2(1H)-one (Example 72, 0.125 g) in ethanol (4 mL) was added sodium borohydride (40 mg). After 3 hour at room temperature, additional sodium borohydride (47 mg) was added. After 30 minutes the reaction was quenched with acetone and concentrated. Chromatography on silica gel with a gradient of dichloromethane to 20% methanol in dichloromethane gave 108 mg of the product as a colorless solid.

Workup

  1. customAfter 30 minutes the reaction was quenched with acetone
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0b5fd0fe75c04208b96a7bbb81e0cb3c
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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