Formaldehyde → HCID 58438409、化合物

HRID 401939ノート

反応式

HRID 401939 の反応式
[Cl-].[Cl-].[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:26][CH2:27][CH:28]2[C:33]([F:35])([F:34])[CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH3:6].C=O.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(Cl)Cl>[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:26][CH2:27][CH:28]2[C:33]([F:35])([F:34])[CH2:32][CH2:31][N:30]([CH3:38])[CH2:29]2)=[CH:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:15][CH:14]=1)[CH2:4][CH2:5][CH3:6]

参加物

6

反応物 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86657794HCID 86657794、化合物

生成物 1

HCID 58438409HCID 58438409、化合物収率 64.6%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(4,4-difluoro-piperidin-3-ylmethoxy)-pyridazine dichloride (0.17 mmol, 90 mg), 37% paraformaldehyde (0.4 mmol, 32 mg), and 1 drop of acetic acid in 5 mL of DCM was stirred for 5 min then added sodium triacetoxyborohydride (0.4 mmol, 85 mg) and continued stirring for 0.5 h at room temperature. Quenched with water, solvent was evaporated; the residue was diluted with ethyl acetate, and then washed with saturated NaHCO3 solution, brine. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by column chromatography using 5% methanolic solution of ammonia (2.0 M ammonia in methanol) in DCM to get 3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(4,4-difluoro-1-methyl-piperidin-3-ylmethoxy)-pyridazine (52 mg).

後処理

  1. customQuenched with water, solvent
  2. customwas evaporated
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with saturated NaHCO3 solution, brine
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant residue was purified by column chromatography

出典と根拠

ORDレコード
ord-f3abb8a00af54d9ba0b8ac5a340377c4
出典データセット
uspto-grants-2014_06
特許番号
US08741900B2

反応ノート

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