Sodium Bicarbonate → 5,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one

HRID 1529566ノート

反応式

HRID 1529566 の反応式
Br[CH:2]1[C:8](=O)[CH2:7][CH2:6][CH2:5][N:4]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:3]1=[O:19].[O:20]([CH2:27][C:28]([NH2:30])=[S:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:4]2[CH2:5][CH2:6][CH2:7][C:8]3[N:30]=[C:28]([CH2:27][O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[S:29][C:2]=3[C:3]2=[O:19])=[CH:12][CH:13]=1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 27460502-PhenoxyethanethioamideHCID 666132613-bromodihydro-1-[(4-methoxyphenyl)methyl]-1H-azepine-2,4(3H,5H)-dione

生成物 1

HCID 666085925,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one収率 68.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-bromodihydro-1-[(4-methoxyphenyl)methyl]-1H-azepine-2,4(3H,5H)-dione (0.78 g, 2.38 mmol) and 2-phenoxythioacetamide (0.36 g, 2.14 mmol) in DMF (12.5 mL) was stirred at room temperature for 15 minutes. Then NaHCO3 (0.32 g, 3.81 mmol) was added and the reaction was stirred at 100° C. for 30 minutes. The reaction was diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; DCM in Heptane 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo to yield 5,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.58 g, 62% yield) as an orange oil. C22H22N2O3S LCMS: Rt 3.01, m/z 395 [M+H]+ (using method, LC-MS Method 6).

後処理

  1. stirringthe reaction was stirred at 100° C. for 30 minutes
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo
  7. customThe crude product was purified by flash column chromatography (silica; DCM in Heptane 0/100 to 100/0)
  8. customThe desired fractions were collected
  9. customthe solvents evaporated in vacuo

出典と根拠

ORDレコード
ord-648d1da1eb0045acb315d9620d65c31c
出典データセット
uspto-grants-2015_07
特許番号
US09090632B2

反応ノート

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