Diisopropylethylamine → 4-(4-Ethyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-6-ylamino)-phenyl]-3-trifluoromethyl-benzamide

HRID 422030노트

반응식

HRID 422030 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH2:13][C:14](=[O:18])[NH:15]3)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[CH2:20]([N:22]1[CH2:27][CH2:26][N:25]([CH2:28][C:29]2[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][C:30]=2[C:38]([F:41])([F:40])[F:39])[CH2:24][CH2:23]1)[CH3:21].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:20]([N:22]1[CH2:23][CH2:24][N:25]([CH2:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]4[CH:17]=[C:16]5[C:12]([CH2:13][C:14](=[O:18])[NH:15]5)=[CH:11][CH:10]=4)[CH:3]=3)=[O:34])=[CH:31][C:30]=2[C:38]([F:41])([F:39])[F:40])[CH2:26][CH2:27]1)[CH3:21]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593970496-((3-Aminophenyl)amino)indolin-2-oneHCID 666744514-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzoic acid hydrochloride

생성물 1

HCID 598043444-(4-Ethyl-piperazin-1-ylmethyl)-N-[3-(2-oxo-2,3-dihydro-1H-indol-6-ylamino)-phenyl]-3-trifluoromethyl-benzamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-(3-amino-phenylamino)-1,3-dihydro-indol-2-one (120 mg, 0.50 mmol, prepared as described in Example 1) and 4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-benzoic acid hydrochloride (213 mg, 0.60 mmol) in DMF (5 mL) is added N,N-diisopropylethylamine (437 μL, 2.5 mmol) followed by addition of HATU (191 mg, 0.50 mmol). The mixture is stirred at ambient temperature overnight. The mixture is diluted with EtOAc and washed with 10% Na2S2O3 aqueous solution and brine. The organic layer is separated, dried over MgSO4, and concentrated. The crude is purified by column chromatography (CH2Cl2/CH3OH=9:1) to give the desired compound. LC-MS: 538.2 (MH+).

후처리

  1. washwashed with 10% Na2S2O3 aqueous solution and brine
  2. customThe organic layer is separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude is purified by column chromatography (CH2Cl2/CH3OH=9:1)

출처 및 근거

ORD 기록
ord-1051cadaf7b14880899f76e049c85222
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101608B2

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