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1,5-Dibromopentane → cyclopropyl-(6-methyl-4-piperidin-1-yl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-methanone

HRID 133544
ノート
印刷プレビュー

反応式

HRID 133544 の反応式
[NH2:1][C:2]1[C:10]2[C:9]3[CH2:11][CH2:12][CH2:13][C:8]=3[S:7][C:6]=2[N:5]=[C:4]([CH3:14])[C:3]=1[C:15]([CH:17]1[CH2:19][CH2:18]1)=[O:16].[H-].[Na+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>CN(C=O)C>[CH:17]1([C:15]([C:3]2[C:4]([CH3:14])=[N:5][C:6]3[S:7][C:8]4[CH2:13][CH2:12][CH2:11][C:9]=4[C:10]=3[C:2]=2[N:1]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:16])[CH2:19][CH2:18]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81001,5-DibromopentaneHCID 24758Sodium hydrideHCID 68896523(4-amino-6-methyl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-cyclopropyl-methanone

生成物 1

HCID 11688694cyclopropyl-(6-methyl-4-piperidin-1-yl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-methanone収率 54%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

実験手順

To a stirred solution of 12 mg (0.044 mmol) of (4-amino-6-methyl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-cyclopropyl-methanone in 2 ml DMF was added 3.0 mg (0.066 mmol) NaH (55% in oil). After 20 minutes, 10 □l (0.044 mmol) of 1,5-dibromo-pentane and stirring was continued at RT over the night. The mixture was poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 6:1) afforded 8 mg (54%) cyclopropyl-(6-methyl-4-piperidin-1-yl-2,3-dihydro-1H-8-thia-7-aza-cyclopenta[a]inden-5-yl)-methanone as a white solid. ES-MS m/e (%): 341 (M+H+, 100).

後処理

  1. customwas continued at RT over the night
  2. additionThe mixture was poured onto water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-34056c9d4db34264a74cc4456791b51e
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07390903B2

反応ノート

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