Sodium borohydride → HCID 58998410, compound

HRID 1593069Notes

Reaction equation

HRID 1593069 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:24][C:25]([NH:27][S:28]([C:31]2[S:32][C:33]([Cl:36])=[CH:34][CH:35]=2)(=[O:30])=[O:29])=[O:26])[CH:7]=[CH:8][C:9]=1[N:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][C:14]([F:22])=[C:15]([NH:20][CH3:21])[CH:16]=2)[C:11]1=[O:23])(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[Cl:36][C:33]1[S:32][C:31]([S:28]([NH:27][C:25]([NH:24][C:6]2[CH:7]=[CH:8][C:9]([N:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][C:14]([F:22])=[C:15]([NH:20][CH3:21])[CH:16]=4)[C:11]3=[O:23])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=2)=[O:26])(=[O:29])=[O:30])=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58998412HCID 58998412, compound2×

Product 1

HCID 58998410HCID 58998410, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

This analog compound was obtained from reduction of N-[({3-acetyl-4-[7-fluoro-6-(methylamino)-1-oxoisoquinolin-2(1H)-yl]phenyl}amino)carbonyl]-5-chlorothiophene-2-sulfonamide of Example 70. To a solution of N-[({3-acetyl-4-[7-fluoro-6-(methylamino)-1-oxoisoquinolin-2(1H)-yl]phenyl}amino)carbonyl]-5-chlorothiophene-2-sulfonamide (18 mg, 0.033 mmol) in 2 mL ethanol, was added sodium borohydride (20 mg, 0.53 mmol). The mixture was stirred at room temperature for 30 minutes. Workup and purification provided 5-chloro-N-({[4-[7-fluoro-6-(methylamino)-1-oxoisoquinolin-2(1H)-yl]-3-(1-hydroxyethyl)phenyl]amino}carbonyl)thiophene-2-sulfonamide as a mixture of rotamers. ES-MS (M+H)+=551, 553(Cl).

Workup

  1. customWorkup and purification

Sources & evidence

ORD record
ord-eab5c27dccce43d7bedd4b1edda448e3
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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