Diisopropylethylamine → 4-[3-(4-Chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid imidazo[1,2-a]pyridin-5-ylamide

HRID 331121

반응식

HRID 331121 반응식
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([NH2:10])=[CH:8][CH:7]=[CH:6][C:5]=12.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:13](=[O:14])C1.Cl.[Cl:30][C:31]1[CH:50]=[CH:49][C:34]([O:35][C:36]2[CH:37]=[C:38]([CH:46]=[CH:47][CH:48]=2)[CH2:39][N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:33][CH:32]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([NH:10][C:13]([N:43]3[CH2:44][CH2:45][N:40]([CH2:39][C:38]4[CH:46]=[CH:47][CH:48]=[C:36]([O:35][C:34]5[CH:49]=[CH:50][C:31]([Cl:30])=[CH:32][CH:33]=5)[CH:37]=4)[CH2:41][CH2:42]3)=[O:14])=[CH:8][CH:7]=[CH:6][C:5]=12

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 327952Imidazo[1,2-a]pyridin-5-amineHCID 676246Di(succinimido) carbonateHCID 674138091-[3-(4-Chloro-phenoxy)-benzyl]-piperazine hydrochloride

생성물 1

HCID 462344674-[3-(4-Chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid imidazo[1,2-a]pyridin-5-ylamide수율 46.4%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of imidazo[1,2-a]pyridin-5-ylamine (56.0 mg, 0.421 mmol) in CH2Cl2 (2.0 mL) were added N,N′-disuccinimidyl carbonate (108 mg, 0.421 mmol) and DMAP (51.0 mg, 0.417 mmol). The reaction mixture was stirred at rt for 6 h, then treated with 1-[3-(4-chloro-phenoxy)-benzyl]-piperazine hydrochloride (158 mg, 0.420 mmol) and diisopropylethylamine (109 mg, 0.840 mmol) and stirred for an additional 16 h at rt. The reaction mixture was diluted with EtOAc and extracted with H2O then saturated aqueous NaCl. The organic layer was dried (MgSO4), and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give 4-[3-(4-chloro-phenoxy)-benzyl]-piperazine-1-carboxylic acid imidazo[1,2-a]pyridin-5-ylamide (90.0 mg, 46%). MS (ESI+): calcd for C26H24ClN6O2 m/z 461.17, found 462.2 (M+H)+. 1H NMR (d6-DMSO): 9.21 (br s, 1H), 7.57 (s, 1H), 7.54 (d, J=1.2, 1H), 7.47-7.35 (m, 4H), 7.23 (dd, J=9.0, 7.2, 1H), 7.15 (d, J=7.6, 1H), 7.06-7.01 (m, 3H), 6.94 (dd, J=8.1, 1.9, 1H), 6.73 (d, J=7.1, 1H), 3.54 (s, 2H), 3.52-3.45 (m, 4H), 2.46-2.40 (m, 4H).

후처리

  1. stirringstirred for an additional 16 h at rt
  2. extractionextracted with H2O
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC, 2 N NH3 in MeOH/DCM)

출처 및 근거

ORD 기록
ord-fb08eda383d9466e829995a891fcdd22
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877769B2

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