Borane;tetrahydrofuran → 4-((S)-2-Fluoro-1-methyl-ethyl)-N-(3-propylamino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)-benzenesulfonamide

HRID 870375Notes

Reaction equation

HRID 870375 reaction equation
[F:1][CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:16]=[C:17]3[O:24][CH2:23][CH:22]([NH:25][C:26](=O)[CH2:27][CH3:28])[CH2:21][C:18]3=[N:19][CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH3:4].B.C1COCC1>C1COCC1>[F:1][CH2:2][C@H:3]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[CH:16]=[C:17]3[O:24][CH2:23][CH:22]([NH:25][CH2:26][CH2:27][CH3:28])[CH2:21][C:18]3=[N:19][CH:20]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)[CH3:4]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68916577N-{7-[4-((S)-2-Fluoro-1-methyl-ethyl)-benzenesulfonylamino]-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl}-propionamide

Product 1

HCID 689126374-((S)-2-Fluoro-1-methyl-ethyl)-N-(3-propylamino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)-benzenesulfonamideYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure as described in example 34, N-{7-[4-((S)-2-fluoro-1-methyl-ethyl)-benzenesulfonylamino]-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl}-propionamide (100 mg, 0.27 mmol) in THF (15 ml) was treated with 1M BH3.THF (2.3 ml, 2.3 mmol). Purification of the crude product by flash column chromatography (CH2Cl2:methanol, 97:3) gave the title compound (50 mg, 52%) as a white solid.

Workup

  1. customPurification of the crude product by flash column chromatography (CH2Cl2:methanol, 97:3)

Sources & evidence

ORD record
ord-6e59cfe6355a4571837a693cf3ff8e3b
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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