1,2-Dichloroethane → N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}-1H-pyrrole-2-carboxamide

HRID 908258노트

반응식

HRID 908258 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][NH:7][CH2:8][C:9]1[N:10]=[C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]2[CH:21]=1.[F:22][C:23]1[CH:38]=[C:37]([F:39])[CH:36]=[C:35]([F:40])[C:24]=1[C:25]([C:27]1[CH:28]=[C:29]([C:32](O)=[O:33])[NH:30][CH:31]=1)=[O:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CCOC(C)=O.CN(C=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[CH2:6][N:7]([CH2:8][C:9]1[N:10]=[C:11]2[CH:16]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:14]=[CH:13][N:12]2[CH:21]=1)[C:32]([C:29]1[NH:30][CH:31]=[C:27]([C:25](=[O:26])[C:24]2[C:23]([F:22])=[CH:38][C:37]([F:39])=[CH:36][C:35]=2[F:40])[CH:28]=1)=[O:33]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 534025784-(2,4,6-Trifluorobenzoyl)-1H-pyrrole-2-carboxylic acidHCID 580248001-(1,3-dioxolan-2-yl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}methanamine

생성물 1

HCID 58024797N-(1,3-dioxolan-2-ylmethyl)-4-(2,4,6-trifluorobenzoyl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}-1H-pyrrole-2-carboxamide수율 35.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a DMF 10 mL solution of 1-(1,3-dioxolan-2-yl)-N-{[7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methyl}methanamine (1.13 g, 3.75 mmol) were added 4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxylic acid (1.06 g, 3.94 mmol), EDC (1.08 g, 5.63 mmol), HOBt (862 mg, 5.63 mmol) and triethyl amine (1.57 mL, 11.25 mmol). The mixture was stirred at room temperature overnight. The resulting suspension was diluted with EtOAc. The organic phase was washed with sat. ammonium chloride aq., sat. aq. sodium bicarbonate aq. and brine, dried over anhydrous Na2SO4, filtered, concentrated and chromatographed on silica gel eluting with a gradient solvent mixture (100% DCM to 5% MeOH-DCM) to give the title compound as foam (744 mg). LC/MS: m/z 533(M+H).

후처리

  1. washThe organic phase was washed with sat. ammonium chloride aq., sat. aq. sodium bicarbonate aq. and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel eluting with a gradient solvent mixture (100% DCM to 5% MeOH-DCM)

출처 및 근거

ORD 기록
ord-fe4f68fc376e402fbefd3cd6d910a3d3
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017605B2

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