4-Toluenesulfonyl chloride → HCID 58970372, 화합물

HRID 2366665노트

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HRID 2366665 반응식
[CH3:1][C:2]([CH3:23])([CH2:6][N:7]1[C:19]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=[CH:11][C:10]=2[N:9]=[C:8]1[CH2:20][CH2:21][CH3:22])[C:3]([NH2:5])=[O:4].C1C=C(Cl)C=C(C(OO)=O)C=1.[OH-].[NH4+:36].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[NH2:36][C:11]1[C:10]2[N:9]=[C:8]([CH2:20][CH2:21][CH3:22])[N:7]([CH2:6][C:2]([CH3:23])([CH3:1])[C:3]([NH2:5])=[O:4])[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

참가 물질

5

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acid2회HCID 57447058HCID 57447058, 화합물

생성물 1

HCID 58970372HCID 58970372, 화합물

반응 조건

온도
0 °C

실험 절차

2,2-Dimethyl-3-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)propanamide was treated with mCPBA (3.24 g, 14.4 mmol) followed by ammonium hydroxide (75 mL) and p-toluenesulfonyl chloride (2.5 g, 13 mmol) according to a modification of the method described in Part F of Example 1. The reaction was cooled to 0° C. before the addition of mCPBA. After the addition, the reaction was stirred for 15 minutes at 0° C. and 1.75 hours at ambient temperature. The reaction was not washed prior to the addition of ammonium hydroxide. The amination reaction was stirred for one hour. The crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol), recrystallized from toluene:methanol, dried overnight in a vacuum oven at 80° C., recrystallized from acetonitrile:water, and dried overnight in a vacuum oven at 80° C. to provide 0.553 g of 3-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2,2-dimethylpropanamide as a yellow solid, mp 219-221° C.

후처리

  1. additionAfter the addition
  2. washThe reaction was not washed
  3. additionto the addition of ammonium hydroxide
  4. customThe amination reaction
  5. stirringwas stirred for one hour
  6. customThe crude product was purified by column chromatography on silica gel (eluting with 90:10 dichloromethane:methanol)
  7. customrecrystallized from toluene
  8. dry with materialmethanol, dried overnight in a vacuum oven at 80° C.
  9. customrecrystallized from acetonitrile
  10. dry with materialwater, and dried overnight in a vacuum oven at 80° C.

출처 및 근거

ORD 기록
ord-5d50df1443264736a578e1d051adc0f4
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697873B2

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