Triethylamine → n-[4'-(2,4-Diamino-pyrimidin-5-ylmethyl)-2',6'-diethoxy-biphenyl-3-yl]-methanesulphonamide

HRID 2416338노트

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HRID 2416338 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([O:14][CH2:15][CH3:16])=[CH:12][C:11]([CH2:17][C:18]3[C:19]([NH2:25])=[N:20][C:21]([NH2:24])=[N:22][CH:23]=3)=[CH:10][C:9]=2[O:26][CH2:27][CH3:28])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>CN(C)C=O>[NH2:24][C:21]1[N:20]=[C:19]([NH2:25])[C:18]([CH2:17][C:11]2[CH:12]=[C:13]([O:14][CH2:15][CH3:16])[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:37]([CH3:36])(=[O:39])=[O:38])[CH:3]=3)=[C:9]([O:26][CH2:27][CH3:28])[CH:10]=2)=[CH:23][N:22]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 98646205-(3'-Amino-2,6-diethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine

생성물 1

HCID 22636769n-[4'-(2,4-Diamino-pyrimidin-5-ylmethyl)-2',6'-diethoxy-biphenyl-3-yl]-methanesulphonamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

5-(3′-Amino-2,6-diethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine (228 mg; 0.6 mmol) is dissolved in dimethylformamide (6 ml; dried over a molecular sieve), triethylamine (0.090 ml; 0.66 mmol) is added at room temperature, and the mixture is cooled to 0° C. and a solution of methanesulphonyl chloride (0.051 ml; 0.66 mmol) in dimethylformamide (1.0 ml) is added in the course of 5 minutes. After 1 hour at 0-5° C. the reaction mixture is concentrated and the residue is taken up in water, after which the pH is adjusted to 10 by addition of NH4OH conc. After stirring for 15 minutes the mixture is filtered with suction and the residue is dried under a high vacuum and chromatographed over silica gel (60 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05).

후처리

  1. additionis added at room temperature
  2. concentrationAfter 1 hour at 0-5° C. the reaction mixture is concentrated
  3. additionafter which the pH is adjusted to 10 by addition of NH4OH conc.
  4. filtrationis filtered with suction
  5. customthe residue is dried under a high vacuum
  6. customchromatographed over silica gel (60 g) with methylene chloride/methanol/NH4OH conc. (19/1/0.05)

출처 및 근거

ORD 기록
ord-bc344275c5ad4d4dbb7bd28ba6ee2f3f
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06821980B1

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