Triethylamine → 5-(8-(4-(1,4'-Bipiperidine-1'-carbonyl)phenylamino)imidazo[1,2-a]pyridin-5-yl)isoindolin-1-one

HRID 552395노트

반응식

HRID 552395 반응식
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:16]4[CH:17]=[CH:18][N:19]=[C:15]4[C:14]([NH:20][C:21]4[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=4)=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[CH2:4][NH:3]1.[CH3:30][N:31](C)[C:32]1C=CC(CN)=C[CH:33]=1.[CH2:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])[CH3:42].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=C[C:58]=2N=N1>CN(C)C=O.CCOC(C)=O>[N:43]1([CH:46]2[CH2:33][CH2:32][N:31]([C:25]([C:24]3[CH:23]=[CH:22][C:21]([NH:20][C:14]4[C:15]5[N:16]([CH:17]=[CH:18][N:19]=5)[C:11]([C:7]5[CH:6]=[C:5]6[C:10](=[CH:9][CH:8]=5)[C:2](=[O:1])[NH:3][CH2:4]6)=[CH:12][CH:13]=4)=[CH:29][CH:28]=3)=[O:26])[CH2:30][CH2:47]2)[CH2:44][CH2:45][CH2:58][CH2:42][CH2:41]1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 808264-(Aminomethyl)-N,N-dimethylanilineHCID 2724699PyBOPHCID 575806954-[5-(1-Oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzoic acid

생성물 1

HCID 249896475-(8-(4-(1,4'-Bipiperidine-1'-carbonyl)phenylamino)imidazo[1,2-a]pyridin-5-yl)isoindolin-1-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzoic acid (37.0 mg, 0.096 mmol), 4-dimethylaminobenzylamine (15.91 mg, 0.106 mmol) and triethylamine (10.72 mg, 0.047 mL, 0.106 mmol) in dimethylformamide (0.4 mL) under nitrogen is added benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (55.10 mg, 0.106 mmol). The reaction mixture is then stirred at room temperature for 18 hours. The mixture is then diluted with EtOAc and washed with saturated aqueous NaHCO3. The combined organic layers are dried (MgSO4) and the solvent is removed under reduced. The crude product is purified by reverse phase HPLC to yield the title compound.

후처리

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe combined organic layers are dried (MgSO4)
  3. customthe solvent is removed
  4. customThe crude product is purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-dc7734a89d844ac084dc0fa1c71483da
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951818B2

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