N,N-Diethyl-2-propanamine → (S)-N-(1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide

HRID 1755271노트

반응식

HRID 1755271 반응식
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=O)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.N1C=N[N:19]2[C:24]([N:25]3[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26]3)=[CH:23][N:22]=[CH:21][C:20]=12.[CH2:31]([N:33](CC)C(C)C)[CH3:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[N:33]1[CH:31]=[CH:32][N:22]2[CH:21]=[CH:20][N:19]=[C:24]([N:25]3[CH2:29][CH2:28][C@H:27]([NH:30][C:12]([C:9]4[N:8]=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[O:11][N:10]=4)=[O:14])[CH2:26]3)[C:23]=12

참가 물질

7

반응물 4

HCID 521913N,N-Diethyl-2-propanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218070875-Phenyl-1,2,4-oxadiazole-3-carboxylic acidHCID 86720545(S)-1-([1,2,4]triazolo[1,5-a]pyrazin-5-yl)pyrrolidin-3-amine hydrochloride salt

생성물 1

HCID 75202692(S)-N-(1-(imidazo[1,2-a]pyrazin-8-yl)pyrrolidin-3-yl)-5-phenyl-1,2,4-oxadiazole-3-carboxamide수율 23.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of the above 5-phenyl-1,2,4-oxadiazole-3-carboxylic acid (58 mg, 0.3 mmol), (S)-1-([1,2,4]triazolo[1,5-a]pyrazin-5-yl)pyrrolidin-3-amine hydrochloride salt (90 mg, 0.32 mmol) in DMF (5 mL) was added diethylisopropyl amine (650 mg, 5 mmol), followed by HATU (120 mg, 0.31 mmol). The resulting solution was stirred at room temperature for 1 h. The reaction mixture was then diluted with ethyl acetate and washed with saturated aqueous solutions of KH2PO4 and NaHCO3, followed by brine. The organic layer was concentrated in vacuo and the residue was purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent) to give 26 mg of the title compound (23% yield) as a white solid. MS: (ES) m/z found 376.2.

후처리

  1. washwashed with saturated aqueous solutions of KH2PO4 and NaHCO3
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residue was purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent)

출처 및 근거

ORD 기록
ord-70dd2a955ba549e7b0ee73f7559e2587
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169261B2

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