Acetic Acid → HCID 69433407, compound

HRID 1270003Notes

Reaction equation

HRID 1270003 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(O)(=O)C.[CH3:13][C:14]1[C:22]([O:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH2:30])[CH2:25]2)=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][NH:18]2.C([BH3-])#N.[Na+].[OH-].[Na+]>>[CH3:13][C:14]1[C:22]([O:23][C@@H:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][CH2:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[CH2:25]2)=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[N:17][NH:18]2

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 69431191HCID 69431191, compound

Product 1

HCID 69433407HCID 69433407, compoundYield 43%

Procedure

Isonicotinaldehyde (42.8 μl, 0.45 mmol) and acetic acid (0.23 mL, 4.08 mmol) were added to a methanolic solution (5 ml) of the cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexanamine (100 mg, 0.41 mmol) obtained in Example 411, and the resulting mixture was stirred for 10 minutes. Then, sodium cyanoborohydride (28.2 mg, 0.45 mmol) was added thereto and stirred for 2 hours. An 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 (ethyl acetate, methanol (5% aqueous ammonia): chloroform=10/100) to obtain N-{cis-3-[(4-methyl-1H-indazol-5-yl)oxy]cyclohexyl}-N-(pyridin-4-ylmethyl)amine (58.7 mg, 43%).

Workup

  1. stirringstirred for 2 hours
  2. extractionfollowed by extraction with chloroform (three times)
  3. dry with materialthe extract solution was dried over anhydrous magnesium sulfate
  4. customThe residue was purified by a silica gel chromatography (ethyl acetate, methanol (5% aqueous ammonia): chloroform=10/100)

Sources & evidence

ORD record
ord-648ce1009e804bcd8b5bc03fe47a4b0b
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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