Borane;tetrahydrofuran → 4-Isopropyl-N-(3-propylamino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)benzenesulfonamide

HRID 870374Notes

Reaction equation

HRID 870374 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]3[O:23][CH2:22][CH:21]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:20][C:17]3=[N:18][CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B.C1COCC1>C1COCC1>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]3[O:23][CH2:22][CH:21]([NH:24][CH2:25][CH2:26][CH3:27])[CH2:20][C:17]3=[N:18][CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68912533N-[7-(4-isopropylbenzenesulfonylamino)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl]-propionamide

Product 1

HCID 116610744-Isopropyl-N-(3-propylamino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)benzenesulfonamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the same procedure as described in example 34, N-[7-(4-isopropylbenzenesulfonylamino)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl]-propionamide (85 mg, 0.21 mmol) in THF (10 ml) was treated with 1M BH3.THF (2.1 ml, 2.1 mmol). Purification of the crude product by flash column chromatography (CH2Cl2:methanol, 97:3) gave the title compound (50 mg, 61%) as a white amorphous solid.

Workup

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

Sources & evidence

ORD record
ord-4afc4b60c2964008a3c612d4bbc131ef
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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