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 908258Notes

Reaction equation

HRID 908258 reaction equation
[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]

Participants

8

Reactant 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

Product 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-carboxamideYield 35.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-fe4f68fc376e402fbefd3cd6d910a3d3
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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