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1,2-Dichloroethane → N,N-dimethyl-2-{[7-oxo-3-(2,4,6-trifluorobenzoyl)-1,7-dihydro-6H-pyrrolo[2,3-c]pyridin-6-yl]methyl}imidazo[1,2-a]pyridine-7-carboxamide

HRID 908264
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HRID 908264 반응식
[O:1]=[C:2]1[C:7]2[NH:8][CH:9]=[C:10]([C:11](=[O:21])[C:12]3[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:13]=3[F:20])[C:6]=2[CH:5]=[CH:4][N:3]1[CH2:22][C:23]1[N:24]=[C:25]2[CH:30]=[C:29]([C:31]([OH:33])=O)[CH:28]=[CH:27][N:26]2[CH:34]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:49][NH:50][CH3:51]>CN(C=O)C.CC#N>[CH3:49][N:50]([CH3:51])[C:31]([C:29]1[CH:28]=[CH:27][N:26]2[CH:34]=[C:23]([CH2:22][N:3]3[CH:4]=[CH:5][C:6]4[C:10]([C:11](=[O:21])[C:12]5[C:13]([F:20])=[CH:14][C:15]([F:19])=[CH:16][C:17]=5[F:18])=[CH:9][NH:8][C:7]=4[C:2]3=[O:1])[N:24]=[C:25]2[CH:30]=1)=[O:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 445467282-{[7-oxo-3-(2,4,6-trifluorobenzoyl)-1,7-dihydro-6H-pyrrolo[2,3-c]pyridin-6-yl]methyl}imidazo[1,2-a]pyridine-7-carboxylic acid

생성물 1

HCID 44517829N,N-dimethyl-2-{[7-oxo-3-(2,4,6-trifluorobenzoyl)-1,7-dihydro-6H-pyrrolo[2,3-c]pyridin-6-yl]methyl}imidazo[1,2-a]pyridine-7-carboxamide
수율 62.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

To the product obtained in Example 23 (4.7 mg, 0.010 mmol) in DMF were added EDC (2.51 mg, 0.013 mmol), HOBt (2.06 mg, 0.013 mmol) and dimethylamine (3.83 μL, 0.030 mmol). After stirring at room temperature overnight, the reaction mixture was diluted with 3:2 MeCN:H2O (2 mL) and purified by reverse phase HPLC (C-18 column) to give the title compound (3.1 mg). LC/MS: m/z 494(M+H). 1H-NMR (500 MHz, d6-DMSO): δ 2.92 (s, 3H), 2.99 (s, 3H), 5.43 (s, 2H), 6.99 (d, 1H), 7.15 (d, 1H), 7.33 (t, 2H), 7.58 (d, 1H), 7.73 (s, 1H), 7.89 (d, 1H), 8.03 (s, 1H), 8.66 (d, 1H), 13.1 (d, 1H).

후처리

  1. customH2O (2 mL) and purified by reverse phase HPLC (C-18 column)

출처 및 근거

ORD 기록
ord-f5ee1ae17eb844078573ead74c2f3296
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017605B2

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