Formaldehyde → HCID 54320050, compound

HRID 1416975Notes

Reaction equation

HRID 1416975 reaction equation
[CH2:1]=O.[CH2:3]([O:7][C:8]1[C:13]([CH2:14]N)=[CH:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[C:10]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:9]=1)[CH2:4][CH2:5][CH3:6].[C:33]([BH3-])#[N:34].[Na+]>C(#N)C.C(O)(=O)C>[CH2:3]([O:7][C:8]1[C:13]([CH2:14][N:34]([CH3:33])[CH3:1])=[CH:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[C:10]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)[N:9]=1)[CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 70274730HCID 70274730, compound

Product 1

HCID 54320050HCID 54320050, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

Aqueous 37% formaldehyde (1 ml) was added to a stirring solution of 2-butoxy-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine-3-methylamine [Example 32] (250 mg, 0.58 mmol) in 5 ml acetonitrile. Sodium cyanoborohydride (54 mg, 0.875 mmol) was added and the reaction mixture was stirred for 15 minutes. Two drops of acetic acid was added and the reaction mixture was stirred for 2 hours. The reaction mixture was concentrated to a paste and the titled material was purified by silica gel chromatography. Anal Calc'd. C25H29N2O3SF+0.25 H2O: C, 65.12; H, 6.45; N, 6.08. Found: C, 65.12; H, 6.46; N, 6.19.

Workup

  1. stirringthe reaction mixture was stirred for 2 hours
  2. concentrationThe reaction mixture was concentrated to a paste
  3. customthe titled material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-17b286681275449ea62ccae60a530092
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

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