Formaldehyde → HCID 58042837, compound

HRID 564180Notes

Reaction equation

HRID 564180 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]3[CH:28]=[CH:27][C:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:20]=4[CH:19]=3)[C:12](=[O:29])[CH:11]=2)=[N:6][CH:7]=1.C=O.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([CH2:16][CH2:17][C:18]3[CH:28]=[CH:27][C:21]4[CH2:22][CH2:23][N:24]([CH3:32])[CH2:25][CH2:26][C:20]=4[CH:19]=3)[C:12](=[O:29])[CH:11]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67007741HCID 67007741, compound

Product 1

HCID 58042837HCID 58042837, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 60 mg (0.13 mmol) 4-(5-bromo-pyridin-2-ylmethoxy)-1-[2-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-ethyl]-1H-pyridin-2-one (example 23.15) in 5.0 mL THF is added 43 μL (0.53 mmol) aqueous 37% formaldehyde solution and 56 mg (0.26 mmol) sodium triacetoxy-borohydride. The mixture is acidified with pH 5 buffer solution and is stirred 48 h at RT. After filtration is the residue purified via reverse HPLC chromatography (Waters Xbridge; water (0.30% NH4OH)/acetonitrile (0.30% NH4OH) 95:5 to 5:95).

Workup

  1. filtrationAfter filtration
  2. custompurified via reverse HPLC chromatography (Waters Xbridge; water (0.30% NH4OH)/acetonitrile (0.30% NH4OH) 95:5 to 5:95)

Sources & evidence

ORD record
ord-2399316e09394816b3a0a032fdf66899
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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