HCID 44223172, compound → HCID 44223225, compound

HRID 2196654Notes

Reaction equation

HRID 2196654 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:36])[C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([NH:18][C:19](=[O:35])[C:20]4[C:25]([F:26])=[CH:24][CH:23]=[C:22]([NH:27][S:28]([CH2:31][CH2:32][CH3:33])(=[O:30])=[O:29])[C:21]=4[F:34])[CH:16]=3)[NH:11][CH:10]=2)=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([NH:18][C:19](=[O:35])[C:20]4[C:25]([F:26])=[CH:24][CH:23]=[C:22]([NH:27][S:28]([CH2:31][CH2:32][CH3:33])(=[O:30])=[O:29])[C:21]=4[F:34])[CH:16]=3)[NH:11][CH:10]=2)=[O:36])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 44223172HCID 44223172, compound

Product 1

HCID 44223225HCID 44223225, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

MnO2 (0.016 g, 0.19 mmol) was added to N-(3-((4-chlorophenyl)(hydroxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.004 g, 0.0075 mmol) in CHCl3 (0.2 mL). The reaction mixture was stirred at room temperature for 60 hours. The contents were filtered through a plug of silica to afford N-(3-(4-chlorobenzoyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (1 mg, 25%) as a solid. 1H NMR (400 MHz, CD3OD) δ 8.94-8.94 (m, 1H), 8.68-8.60 (m, 1H), 8.04 (s, 1H), 7.83-7.86 (m, 2H), 7.63-7.69 (m, 1H), 7.56-7.58 (m, 2H), 7.11-7.17 (m, 1H), 3.10-3.14 (m, 2H), 1.85-1.90 (m, 2H), 1.04-1.08 (m, 3H); m/z (APCI-neg) M−1=531.2.

Workup

  1. filtrationThe contents were filtered through a plug of silica

Sources & evidence

ORD record
ord-36494ff87c764802aafe0c188b8a873e
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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