Triethylamine → 2-chloro-N-(5-ethyl-1,3,4-oxadiazol-2-yl)-6-(trifluoromethyl)nicotinamide

HRID 511740노트

반응식

HRID 511740 반응식
[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:15]([C:17]1[O:21][C:20]([NH2:22])=[N:19][N:18]=1)[CH3:16].C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:22][C:20]1[O:21][C:17]([CH2:15][CH3:16])=[N:18][N:19]=1)=[O:6]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 3434875-Ethyl-1,3,4-oxadiazol-2-amineHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acid

생성물 1

HCID 867124952-chloro-N-(5-ethyl-1,3,4-oxadiazol-2-yl)-6-(trifluoromethyl)nicotinamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

200 mg (0.887 mmol) of 2-chloro-6-(trifluoromethyl)nicotinic acid and 100 mg (0.887 mmol) of 5-ethyl-1,3,4-oxadiazol-2-amine are dissolved at RT in 8 ml of CH2Cl2. Then 846 mg (1.33 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added, the mixture is stirred at RT for one hour and then 0.618 ml (4.43 mmol) of triethylamine, 22 mg (0.177 mmol) of 4-dimethylaminopyridine are added. The reaction mixture is stirred at RT for 20 h and then washed twice with 4 ml each time of water, dried over sodium sulfate and concentrated. The residue is purified by column chromatography (prep. HPLC; acetonitrile/water). Yield 80 mg (28%).

후처리

  1. stirringThe reaction mixture is stirred at RT for 20 h
  2. washwashed twice with 4 ml each time of water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography (prep. HPLC; acetonitrile/water)

출처 및 근거

ORD 기록
ord-3314f49db5f94175a762261a6a9c71c7
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09101141B2

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