3-Chloropropionyl chloride → HCID 22036735, 화합물

HRID 1267059노트

반응식

HRID 1267059 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 22036735HCID 22036735, 화합물수율 99%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 241Benzene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d6ca66c5ed81429abcd25eed95671a2b
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552017B1

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