Tetrahydrofuran → HCID 66707832, 화합물

HRID 1691342노트

반응식

HRID 1691342 반응식
[C:1]([C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[C:10]1([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24]C(Cl)=NO)=CC=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:29]([N:31](CC)CC)[CH3:30].[O:36]1CCCC1>>[C:17]1([S:16][C:10]2[CH:11]=[CH:12][C:13]([CH2:30][C:29]3[CH:2]=[C:1]([C:3]4[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=4)[O:36][N:31]=3)=[CH:14][CH:15]=2)[CH:18]=[CH:23][CH:22]=[CH:21][CH:24]=1

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 124225263-Ethynylpyridin-2-amineHCID 72262853(4-Phenylsulfanylmethyl-phenyl)acetohydroximoyl chloride

생성물 1

HCID 66707832HCID 66707832, 화합물수율 26%

실험 절차

To a tetrahydrofuran (3 mL) solution of 3-ethynyl-pyridin-2-ylamine (50 mg, 0.423 mmol) described in Manufacturing Example 1-2-3 and (4-phenylsulfanylmethyl-phenyl)acetohydroximoyl chloride (197 mg, 0.677 mmol) described in Manufacturing Example 206-1-6 was added triethylamine (147 μL, 1.06 mmol), which was stirred for 18 hours at room temperature. The mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 to 1:2) to obtain the title compound (41 mg, 26%).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. custompartitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 to 1:2)

출처 및 근거

ORD 기록
ord-282f864e4370403b8195a21816eb74dc
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

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