Myristoyl chloride → 1-[N-(2-cyanoethyl)tetradecanamido]-5-(4,6-dimethyl-2-pyrimidylamino)-pentane

HRID 34754

반응식

HRID 34754 반응식
[C:1]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[N:13]=1)#[N:2].[C:20](Cl)(=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>N1C=CC=CC=1>[C:1]([CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[N:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[N:17]=1)[C:20](=[O:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])#[N:2]

참가 물질

4

반응물 2

HCID 66986Myristoyl chlorideHCID 143460181-(2-Cyanoethylamino)-5-(4,6-dimethyl-2-pyrimidylamino)pentane

생성물 1

HCID 143460191-[N-(2-cyanoethyl)tetradecanamido]-5-(4,6-dimethyl-2-pyrimidylamino)-pentane

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

Crude XIII was dissolved in dry pyridine to which 1 eq of tetradecanoyl chloride was added with stirring. The run was followed by tlc and excess acid chloride was added to drive the reaction to completion. Ice was then added to quench the reaction followed by the addition of CHCl3. The mixture was first extracted with 10% NaHCO3 and then with 1M HOAc to remove the bulk of the pyridine. The remaining CHCl3 phase was evaporated to yield the crude product which was purified by chromatography on a 100 g silica gel (Brinkman 50-200μ) column developed with 30% acetone/chloroform. The product (1 g) was collected after only 150 ml of eluant had passed through the column and was only partially purified.

후처리

  1. additionwas added
  2. additionwas added
  3. customthe reaction to completion
  4. additionIce was then added
  5. customto quench the reaction
  6. additionfollowed by the addition of CHCl3
  7. extractionThe mixture was first extracted with 10% NaHCO3
  8. customwith 1M HOAc to remove the bulk of the pyridine
  9. customThe remaining CHCl3 phase was evaporated

출처 및 근거

ORD 기록
ord-c8bf72232d3b47c7a1a782d5442b0f34
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762949

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