Formaldehyde → HCID 44199248, compound

HRID 79570Notes

Reaction equation

HRID 79570 reaction equation
C=O.[BH3-][C:4]#N.[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]([CH2:38][NH:39][CH:40]([CH3:42])[CH3:41])[C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:27][N:26]=[C:25]4[NH:35][CH:36]=[CH:37][C:24]=34)[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1.C([O-])(O)=O.[Na+]>CO>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]([CH2:38][N:39]([CH:40]([CH3:42])[CH3:41])[CH3:4])[C:15]([N:17]2[CH2:18][CH2:19][N:20]([C:23]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:27][N:26]=[C:25]4[NH:35][CH:36]=[CH:37][C:24]=34)[CH2:21][CH2:22]2)=[O:16])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 44198998(S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one

Product 1

HCID 44199248HCID 44199248, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Formaldehyde (0.0712 mL, 0.957 mmol) and NaCNBH3 (0.0120 g, 0.191 mmol) were added to (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (0.055 g, 0.096 mmol, see Example 13) in MeOH (0.5 mL). The mixture was stirred at room temperature for 20 minutes. Saturated NaHCO3 (5 mL) was added, the aqueous layer was extracted with DCM (20 mL), and the combined organic phases were dried over sodium sulfate. After removal of the solvent, the residue was purified by chromatography (20:1:0.1 DCM:ethyl acetate:ammonium hydroxide) to give (S)-2-(4-chlorophenyl)-3-(isopropyl(methyl)amino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (0.013 g, 23%) as a solid. MS ESI (+) m/z 516 detected.

Workup

  1. extractionthe aqueous layer was extracted with DCM (20 mL)
  2. dry with materialthe combined organic phases were dried over sodium sulfate
  3. customAfter removal of the solvent
  4. customthe residue was purified by chromatography (20:1:0.1 DCM:ethyl acetate:ammonium hydroxide)

Sources & evidence

ORD record
ord-07c6db655e4c4a2995b8bcdd30a8446d
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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