Potassium Carbonate → 5-(2-(4-((2'-Chloro-4',4'-difluoro-4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran]-1-yl)methyl)-3-methyl-1H-pyrazol-1-yl)pyridin-3-yl)oxazole

HRID 1517606노트

반응식

HRID 1517606 반응식
[Cl:1][C:2]1[S:32][C:5]2[C:6]3([CH2:16][CH2:15][N:14]([CH2:17][C:18]4[C:19]([CH3:31])=[N:20][N:21]([C:23]5[N:30]=[CH:29][CH:28]=[CH:27][C:24]=5[CH:25]=[O:26])[CH:22]=4)[CH2:13][CH2:12]3)[O:7][CH2:8][C:9]([F:11])([F:10])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S([CH2:48][N+:49]#[C-:50])(=O)=O)=CC=1>CO>[Cl:1][C:2]1[S:32][C:5]2[C:6]3([CH2:12][CH2:13][N:14]([CH2:17][C:18]4[C:19]([CH3:31])=[N:20][N:21]([C:23]5[C:24]([C:25]6[O:26][CH:50]=[N:49][CH:48]=6)=[CH:27][CH:28]=[CH:29][N:30]=5)[CH:22]=4)[CH2:15][CH2:16]3)[O:7][CH2:8][C:9]([F:11])([F:10])[C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 582685962-[4-[(2-Chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)methyl]-3-methyl-pyrazol-1-yl]pyridine-3-carbaldehyde

생성물 1

HCID 582686355-(2-(4-((2'-Chloro-4',4'-difluoro-4',5'-dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran]-1-yl)methyl)-3-methyl-1H-pyrazol-1-yl)pyridin-3-yl)oxazole수율 71.8%

시약·촉매·용매 1

HCID 887Methanol용매2회

반응 조건

온도
65 °C

실험 절차

To a screw-cap test tube containing 2-(4-((2′-chloro-4′,4′-difluoro-4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran]-1-yl)methyl)-3-methyl-1H-pyrazol-1-yl)nicotinaldehyde (0.120 g, 0.25 mmol) in methanol (2.5 mL) are added potassium carbonate (0.104 g, 0.75 mmol) and p-toluenesulfonylmethyl isocyanide (0.054 g, 0.28 mmol) under nitrogen. The reaction tube is quickly sealed (caution: build-up of pressure possible; use a safety shield) and is stirred in a preheated oil bath at 65° C. for 3 hr. with the aid of a magnetic stirrer. The mixture is diluted with methanol and purified using a 2 g SCX cartridge. The solvent is evaporated in vacuo. The resulting residue is purified by normal phase Isco chromatography eluting with hexane/ethanol (5-30%) to give 0.093 g of the title compound. MS (m/z): 518 (M+1)

후처리

  1. customThe reaction tube is quickly sealed (caution
  2. custompurified
  3. customThe solvent is evaporated in vacuo
  4. customThe resulting residue is purified by normal phase Isco chromatography
  5. washeluting with hexane/ethanol (5-30%)

출처 및 근거

ORD 기록
ord-e6555a125dba4eac8fa5c2c0007f921f
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232289B2

반응 노트

불러오는 중…