Tert-Butylamine → N-tert-butyl-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridin-2-amine

HRID 45857

反応式

HRID 45857 の反応式
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][N+:16]([O-])=[CH:15][CH:14]=3)[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=3)=[N:9]2)=[CH:5][CH:4]=1.[C:31]([NH2:35])([CH3:34])([CH3:33])[CH3:32].C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>FC(C1C=CC=CC=1)(F)F.ClCCl>[C:31]([NH:35][C:15]1[CH:14]=[C:13]([C:11]2[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=3)=[N:9][N:8]([CH2:7][C:6]3[CH:29]=[CH:30][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:12]=2)[CH:18]=[CH:17][N:16]=1)([CH3:34])([CH3:33])[CH3:32]

参加物

6

反応物 3

HCID 6385Tert-ButylamineHCID 77773Toluene-p-sulphonic anhydrideHCID 671844794-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine 1-oxide

生成物 1

HCID 67185904N-tert-butyl-4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridin-2-amine収率 75%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 7368(Trifluoromethyl)benzene溶媒

実験手順

580 mg (1.44 mmol) of 4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]pyridine 1-oxide were suspended in a mixture of 16 ml of trifluoromethylbenzene and 4 ml of dry dichloromethane and 756 μl of tert-butylamine were added. At 0° C. 936 mg (7.2 mmol) of p-toluensulfonic anhydride were added. After 6 hours under stirring in the same conditions the solvent was removed under reduced pressure, the residue partitioned between dichloromethane and water, the organic layer dried over sodium sulphate and evaporated. The crude was then purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 19/1), giving 500 mg (75%) of the title compound.

後処理

  1. additionwere added
  2. customAt 0° C
  3. customwas removed under reduced pressure
  4. customthe residue partitioned between dichloromethane and water
  5. dry with materialthe organic layer dried over sodium sulphate
  6. customevaporated
  7. customThe crude was then purified by flash-chromatography on a silica gel column (CH2Cl2-CH3COCH3 19/1)

出典と根拠

ORDレコード
ord-2f033fe9e5334c92aff36846eb4e880f
出典データセット
uspto-grants-2013_09
特許番号
US08541575B2

関連ノート

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