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 1517606ノート

反応式

HRID 1517606 の反応式
[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

参加物

5

反応物 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

生成物 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)oxazole収率 71.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
65 °C

実験手順

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)

後処理

  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%)

出典と根拠

ORDレコード
ord-e6555a125dba4eac8fa5c2c0007f921f
出典データセット
uspto-grants-2012_07
特許番号
US08232289B2

反応ノート

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