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

HRID 552395ノート

反応式

HRID 552395 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dc7734a89d844ac084dc0fa1c71483da
出典データセット
uspto-grants-2011_05
特許番号
US07951818B2

反応ノート

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