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 908258ノート

反応式

HRID 908258 の反応式
[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]

参加物

8

反応物 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

生成物 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-carboxamide収率 35.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fe4f68fc376e402fbefd3cd6d910a3d3
出典データセット
uspto-grants-2011_09
特許番号
US08017605B2

反応ノート

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