Acetyl chloride → (4-Chloro-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.0(2),]dodeca-2(6),7-dien-10-yl}pyridin-3-yl)methyl acetate

HRID 592843ノート

反応式

HRID 592843 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:19][CH2:18][N:17]3[C:10](=[CH:11][C:12]4[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]=43)[C:9]2=[O:22])[C:3]=1[CH2:23][OH:24].C(N(CC)CC)C.[C:32](Cl)(=[O:34])[CH3:33]>C1COCC1>[C:32]([O:24][CH2:23][C:3]1[C:4]([N:8]2[CH2:19][CH2:18][N:17]3[C:10](=[CH:11][C:12]4[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15][C:16]=43)[C:9]2=[O:22])=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:34])[CH3:33]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 866843692-(4-chloro-3-(hydroxymethyl)pyridin-2-yl)-7,7-dimethyl-2,3,4,6,7,8-hexahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-1-one

生成物 1

HCID 86684370(4-Chloro-2-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.0(2),]dodeca-2(6),7-dien-10-yl}pyridin-3-yl)methyl acetate収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with 199c (7.0 g, 20.2 mmol, 1.0 eq.), triethylamine (4.08 g, 40.4 mmol, 2.0 eq.), and THF (50 mL). To the mixture was added the solution of acetyl chloride (2.36 g, 30.3 mmol, 1.5 eq.) in THF (20 mL) dropwise. The reaction mixture was stirred at room temperature for one hour. After the reaction was completed, it was quenched with ice water and evaporated under reduced pressure. The residue was extracted with dichloromethane. The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was washed with 1:8 ethyl acetate/petroleum to afford 199d as a white solid (5.9 g, 76%). MS-ESI: [M+H]+ 388.3.

後処理

  1. customA 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customit was quenched with ice water
  3. customevaporated under reduced pressure
  4. extractionThe residue was extracted with dichloromethane
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. washThe resulting residue was washed with 1:8 ethyl acetate/petroleum

出典と根拠

ORDレコード
ord-06ba0e4f8aa24f0f866874c428fe00b9
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

反応ノート

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