Imidazole → 3-(tert-Butyl)-1-(4-(((triisopropylsilyl)oxy)methyl)phenyl)-1H-pyrazol-5-amine

HRID 1427405ノート

反応式

HRID 1427405 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=2)[N:5]=[C:4]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=1.N1C=CN=C1.Cl[Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27]>C1COCC1>[C:15]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[CH:9][CH:8]=2)[N:5]=1)([CH3:18])([CH3:17])[CH3:16]

参加物

5

反応物 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 58532567(4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)methanol

生成物 1

HCID 866877993-(tert-Butyl)-1-(4-(((triisopropylsilyl)oxy)methyl)phenyl)-1H-pyrazol-5-amine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)methanol (Ito, K. et al., WO 2010/067131) (8.50 g, 35.0 mmol) and 1H-imidazole (2.71 g, 39.8 mmol) in dry THF (100 mL) under N2 was added chlorotriisopropylsilane (8.16 mL, 38.1 mmol) and the reaction mixture maintained at RT for 5 days. The resulting mixture was evaporated in vacuo and the residue was partitioned between EtOAc (250 mL) and water (100 mL). The organic layer was separated and was washed with (water (100 mL) and brine (80 mL) and then dried and evaporated in vacuo to afford the title compound, Intermediate A12 as a dark red solid (14.6 g, 97%); Rt 3.26 min (Method 2); m/z 402 (M+H)+, (ES+).

後処理

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc (250 mL) and water (100 mL)
  3. customThe organic layer was separated
  4. washwas washed with (water (100 mL) and brine (80 mL)
  5. customdried
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-03026a035962419d8cfc03f42d457da2
出典データセット
uspto-grants-2015_01
特許番号
US08933228B2

反応ノート

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