Formaldehyde → HCID 67155894, compound

HRID 2196676Notes

Reaction equation

HRID 2196676 reaction equation
[F:1][C:2]1[C:34]([NH:35][S:36]([CH2:39][CH2:40][CH3:41])(=[O:38])=[O:37])=[CH:33][CH:32]=[C:31]([F:42])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([C:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH:21]=3)[N:13]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C:10]2=[N:11][CH:12]=1)=[O:5].[CH2:43](Cl)Cl.CO.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.CC(O)=O>[F:1][C:2]1[C:34]([NH:35][S:36]([CH2:39][CH2:40][CH3:41])(=[O:38])=[O:37])=[CH:33][CH:32]=[C:31]([F:42])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([C:16]3[CH2:17][CH2:18][N:19]([CH3:43])[CH2:20][CH:21]=3)[N:13]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:23])=[O:24])[C:10]2=[N:11][CH:12]=1)=[O:5]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21226129Dichloromethane methanolHCID 67156037HCID 67156037, compound

Product 1

HCID 67155894HCID 67155894, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2,6-difluoro-N-(1-(phenylsulfonyl)-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (15 mg, 0.024 mmol) in 5:1 CH2Cl2/MeOH (6 mL) was treated with 37% aqueous formaldehyde (100 μL) and a drop of AcOH. After 5 minutes, the mixture was treated with sodium triacetoxyborohydride (26 mg, 5 eq.), and the reaction mixture was stirred for 16 hours at ambient temperature. The mixture was treated with MeOH (1 mL), concentrated under reduced pressure, and purified by silica gel chromatography (eluting with 10% MeOH/CH2Cl2) to afford 2,6-difluoro-N-(2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide.

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by silica gel chromatography (eluting with 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ab1681968fca4ea190d5065ef9dd316a
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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