Triethylamine → HCID 178527247, 화합물

HRID 1698944노트

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HRID 1698944 반응식
N[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:20]([N:22](CC)CC)[CH3:21].N1C=CC=CC=1.CNC.ClCC[S:39](Cl)(=[O:41])=[O:40]>O1CCCC1.C([O-])(O)=O.[Na+]>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([CH:21]=[CH:20][NH:22][SH:39](=[O:41])=[O:40])=[CH:3][CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazolineHCID 21954350Dimethylamine pyridine

생성물 1

HCID 178527247HCID 178527247, 화합물수율 12%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of 7-amino-4-[(3-bromophenyl)amino]quinazoline (J Med Chem, 1995;38:3482) (500 mg, 1.59 mmol), triethylamine (Et3N) (0.60 mL) and dimethylamine pyridine (DMAP) (catalytic) in tetrahydrofuran (THF) (30 mL) was reacted with chloroethanesulfonyl chloride (1.6 mol eq., 2.54 mmol, 265 μL) at 25° C. for 1 hour, stirred under N2. The reaction mixture was diluted with saturated NaHCO3 and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, concentrated under reduced pressure, and chromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (3:47:50). Crystallization from CH2Cl2/hexane, gave N-[4-[(3-bromophenyl)amino]quinazolin-7-yl]vinylsulfonamide (80 mg, 12%) as a cream powder, mp 218° C. decomposes (dec).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (3:47:50)
  6. customCrystallization from CH2Cl2/hexane

출처 및 근거

ORD 기록
ord-29f7a604200241ca95d3e92d827b58a4
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344459B1

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