Borohydride → HCID 54575148, compound

HRID 2190158Notes

Reaction equation

HRID 2190158 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:18]([C:19]([NH:21][CH3:22])=[O:20])=[C:17]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[O:16][C:7]2=[N:8][C:9]=1[N:10]([CH3:15])[S:11]([CH3:14])(=[O:13])=[O:12])(=[O:3])[CH3:2].[BH4-]>O1CCCC1>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:17]2[O:16][C:7]3=[N:8][C:9]([N:10]([CH3:15])[S:11]([CH3:14])(=[O:12])=[O:13])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=[C:6]3[C:18]=2[C:19]([NH:21][CH3:22])=[O:20])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 28123BorohydrideHCID 54575090HCID 54575090, compound

Product 1

HCID 54575148HCID 54575148, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-acetyl-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide (3 mg, 7.15 μmol) in tetrahydrofuran (0.1 ml) was added 10 mg of resin-bound borohydride (Aldrich cat#328642, 2.5 mmol BH4/g). After LCMS indicated complete conversion to product, the reaction mixture was filtered and purified by HPLC to afford the title compound (1.5 mg, 50%). MS (ESI) m/z 422.3 (M+1). NMR (400 MHz, CDCl3) δ 8.50 (s, 1H), 8.03-7.99 (m, 2H), 7.26-7.22 (m, 2H), 5.88 (br s, 1H), 5.55-5.53 (m, 1H), 3.37 (s, 3H), 3.13 (s, 3H), 3.06-3.05 (d, 3H), 1.61-1.60 (d, 3H)

Workup

  1. filtrationthe reaction mixture was filtered
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-da72a05f0a3b4fcf914eb0e95581c605
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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