3-Chloropropionyl chloride → HCID 22036735、化合物

HRID 1764817ノート

反応式

HRID 1764817 の反応式
[NH2:1][C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:22][CH2:23][CH2:24][C:25](Cl)=[O:26].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.CN(C1C=CN=CC=1)C>[Cl:22][CH2:23][CH2:24][C:25]([NH:1][C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:26]

参加物

6

反応物 3

HCID 693643-Chloropropionyl chlorideHCID 516892Sodium BicarbonateHCID 22036788tert-Butyl 6-amino-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

生成物 1

HCID 22036735HCID 22036735、化合物収率 99%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 241Benzene溶媒

実験手順

To a solution of tert-butyl 6-amino-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (4.62 g, 16.08 mmol) in benzene (100 mL) was added a catalytic amount of DMAP. An inert atmosphere was created and chloropropionyl chloride (2)(1.68 mL) was added dropwise to the reaction mixture. After stirring at room temperature for 20 min, the reaction mixture was transferred to a separatory funnel containing 50% solution of sodium bicarbonate and was extracted with CH2Cl2 (3×250 mL). The combined organics were dried over Na2SO4 and concentrated in vacuo to give tert-butyl 6-[(3-chloropropanoyl)amino]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate as a white solid in 99% yield: 1H NMR (DMSO, 500 MHz) δ 1.38-1.53 (m, 9H), 2.75-2.99 (m, 2H), 3.65-3.78 (m, 4H), 3.88-3.97 (m, 2H), 4.53 (brs, 2H), 6.88-6.96 (m, 1H), 7.15-7.22 (m, 1H), 7.31-7.37 (m, 1H), 9.72 (brs, 1H), 10.44 (brs, 1H) ppm.

後処理

  1. customthe reaction mixture was transferred to a separatory funnel
  2. extractionwas extracted with CH2Cl2 (3×250 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f1fb0071a8c447f19d7b2c7bfc072045
出典データセット
uspto-grants-2007_06
特許番号
USRE039680E1

反応ノート

読み込み中…