Acetic Acid → HCID 178437278, compound

HRID 1270005Notes

Reaction equation

HRID 1270005 reaction equation
C(O)(=O)C.C=O.[CH2:7]([C:9]1[C:17]([O:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([N:25]3[C:33](=O)C4C(=CC=CC=4)[C:26]3=O)[CH2:21][CH2:20]2)=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][NH:13]2)[CH3:8].C([BH3-])#N.[Na+].[OH-].[Na+]>>[CH2:7]([C:9]1[C:17]([O:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([N:25]([CH3:33])[CH3:26])[CH2:21][CH2:20]2)=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][NH:13]2)[CH3:8]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 178437277HCID 178437277, compound

Product 1

HCID 178437278HCID 178437278, compoundYield 57.3%

Procedure

Acetic acid (0.14 mL, 2.5 mmol) and an aqueous formaldehyde solution (209.3 mg, 2.5 mmol) were added to a methanolic solution (3 mL) of the trans-4-((4-ethyl-1H-indazol-5-yl)oxy)cyclohexanamine (130 mg, 0.5 mmol) obtained in Example 744, and then sodium cyanoborohydride (157.7 mg, 2.5 mmol) was added thereto and stirred overnight. A 1N-aqueous sodium hydroxide solution was added to the reaction solution, followed by extraction with chloroform (three times), and the extract solution was dried over anhydrous magnesium sulfate. The residue was purified by a silica gel chromatography (methanol:chloroform=0/100 to 10/100) to obtain trans-N-{4-[(4-ethyl-1H-indazol-5-yl)oxy]cyclohexyl}-N,N-dimethylamine (82.3 mg, 57%).

Workup

  1. extractionfollowed by extraction with chloroform (three times)
  2. dry with materialthe extract solution was dried over anhydrous magnesium sulfate
  3. customThe residue was purified by a silica gel chromatography (methanol:chloroform=0/100 to 10/100)

Sources & evidence

ORD record
ord-90036e11e15a45d7a9c0e4a6fb98c24d
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…