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

HRID 1694123

반응식

HRID 1694123 반응식
[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

참가 물질

8

반응물 4

HCID 14798Sodium Hydroxide2회HCID 23392Picolyl chloride hydrochlorideHCID 23393Picolyl chlorideHCID 592552174-(5-(2-Amino-6-methoxymethyl-pyridin-3-yl)isoxazol-3-ylmethyl)-phenol

생성물 2

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-fca613e93e15412cbdcbd2b1af133c60
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158657B2

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