Sodium Hydroxide → 6-Methoxymethyl-3-(3-(4-(pyridin-2-ylmethoxy)-benzyl)-isoxazol-5-yl)pyridin-2-ylamine

HRID 1891881

反応式

HRID 1891881 の反応式
[NH2:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[CH:9]=2)=[CH:6][CH:5]=[C:4]([CH2:21][O:22][CH3:23])[N:3]=1.[OH-].[Na+].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][Cl:33].Cl.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41]Cl>O.CO>[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][Cl:33].[CH3:23][O:22][CH2:21][C:4]1[N:3]=[C:2]([NH2:1])[C:7]([C:8]2[O:12][N:11]=[C:10]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:41][C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=4)=[CH:16][CH:15]=3)[CH:9]=2)=[CH:6][CH:5]=1

参加物

8

反応物 4

HCID 14798Sodium Hydroxide2 回HCID 23392Picolyl chloride hydrochlorideHCID 23393Picolyl chlorideHCID 592552174-(5-(2-Amino-6-methoxymethyl-pyridin-3-yl)isoxazol-3-ylmethyl)-phenol

生成物 2

HCID 23393Picolyl chlorideHCID 592552866-Methoxymethyl-3-(3-(4-(pyridin-2-ylmethoxy)-benzyl)-isoxazol-5-yl)pyridin-2-ylamine収率 52%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a methanol (1.5 mL) solution of 4-(5-(2-amino-6-methoxymethyl-pyridin-3-yl)isoxazol-3-ylmethyl)-phenol (50 mg, 0.16 mmol) described in Manufacturing Example 166-1-1 was added a 1 N sodium hydroxide aqueous solution (160 μL, 0.16 mmol), which was concentrated under a reduced pressure. N,N-dimethylformamide (1.5 mL) was added to the residue thus obtained at room temperature, and 2-picolyl chloride (29 mg, 0.23 mmol; this 2-picolyl chloride was prepared by adding a 5 N sodium hydroxide aqueous solution to 2-picolyl chloride hydrochloride) was added to the reaction mixture at the same temperature. The reaction mixture was stirred for 100 minutes at the same temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=4:1) to obtain the title compound (32 mg, 52%).

後処理

  1. concentrationwas concentrated under a reduced pressure
  2. additionN,N-dimethylformamide (1.5 mL) was added to the residue
  3. customthus obtained at room temperature
  4. additionwas added to the reaction mixture at the same temperature
  5. extractionwas extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. concentrationwas concentrated under a reduced pressure
  8. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=4:1)

出典と根拠

ORDレコード
ord-735e0194adc743cb806a88eeb4a07250
出典データセット
uspto-grants-2013_08
特許番号
US08507530B2

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