Borane;tetrahydrofuran → HCID 10271266, compound

HRID 1351510Notes

Reaction equation

HRID 1351510 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([C:25](=O)[N:26]([CH3:28])[CH3:27])[CH:20]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][N:26]([CH3:28])[CH3:27])[CH:20]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 23577285HCID 23577285, compound

Product 1

HCID 10271266HCID 10271266, compound

Procedure

To 4-[(2-Dimethylcarbamoyl-pyridin-4-ylamino)-methyl]-piperidine-1-carboxylic acid benzyl ester (28 mg, 0.05 mmol) was added a solution of 1.0M borane-tetrahydrofuran (2 mL). The reaction was stirred at room temperature for 24 h. The reaction was quenched with 1N HCl (2 mL) and concentrated in vacuo to an oil. Reverse phase chromatography (C-18 using acetonitrile/0.1% trifluoroacetic acid in water) gave upon concentration in vacuo EXAMPLE 51.

Workup

  1. customThe reaction was quenched with 1N HCl (2 mL)
  2. concentrationconcentrated in vacuo to an oil
  3. customReverse phase chromatography (C-18 using acetonitrile/0.1% trifluoroacetic acid in water) gave upon concentration in vacuo EXAMPLE 51

Sources & evidence

ORD record
ord-bef4c78e233c414980a25ffbedafdc8a
Source dataset
uspto-grants-2007_05
Patent number
US07217716B2

Reaction notes

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