Diisopropylethylamine → HCID 58230870, 화합물

HRID 252237

반응식

HRID 252237 반응식
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].CCN(C(C)C)C(C)C.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][C:22]=1[OH:30]>C(Cl)Cl.C1COCC1.C(OCC)(=O)C>[OH:30][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:21]=1[NH:20][C:4]([C:3]1[C:2]([CH3:1])=[N:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[C:25]([OH:27])=[O:26]

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 1375664-Amino-3-hydroxybenzoic acidHCID 129025982-Methylpyridine-3-carbonyl chloride

생성물 1

HCID 58230870HCID 58230870, 화합물수율 40.2%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

2-methyl nicotinoyl chloride (0.2 g, 0.00128 mols) is dissolved in 30 ml dry DCM and N,N′-Diisopropylethylamine (0.994 g, 0.00769 mols) is added slowly to the acid chloride solution at 0° C. under nitrogen atmosphere. A solution of 4-Amino-3-hydroxybenzoic acid (0.196 g, 0.00128 mols) in 10 ml dry THF is slowly added to the above solution at 0° C. The solution is then stirred at 0° C. for 30 mins and then at RT overnight. The reaction mixture is then diluted with 100 ml Ethyl acetate and stirred for 30 mins. The precipitated tarry material is filtered off over celite bed and the organic phase given 4×20 ml water wash, 2×10 ml brine wash dried over sodium sulfate and rotary evaporated to get the crude amide (140 mg) which is taken for the cyclisation step without further purification.

후처리

  1. customat RT
  2. customovernight
  3. stirringstirred for 30 mins
  4. filtrationThe precipitated tarry material is filtered off over celite bed
  5. washwash
  6. wash2×10 ml brine wash
  7. dry with materialdried over sodium sulfate
  8. customrotary evaporated

출처 및 근거

ORD 기록
ord-68113f6b2507438c962f16b003e8b0f2
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868033B2

연결된 노트

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