1,2-Dichloroethane → N-(1H-benzimidazol-2-ylmethyl)-N-(2,2-dimethoxyethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamide

HRID 908252Notes

Reaction equation

HRID 908252 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][NH:11][CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15].[F:18][C:19]1[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[C:20]=1[C:21]([C:23]1[CH:24]=[C:25]([C:28](O)=[O:29])[NH:26][CH:27]=1)=[O:22].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:12][CH:13]([O:14][CH3:15])[O:16][CH3:17])[C:28]([C:25]1[NH:26][CH:27]=[C:23]([C:21](=[O:22])[C:20]2[C:19]([F:18])=[CH:34][C:33]([F:35])=[CH:32][C:31]=2[F:36])[CH:24]=1)=[O:29]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 534025784-(2,4,6-Trifluorobenzoyl)-1H-pyrrole-2-carboxylic acidHCID 58024802N-(1H-benzimidazol-2-ylmethyl)-2,2-dimethoxyethanamine

Product 1

HCID 58024795N-(1H-benzimidazol-2-ylmethyl)-N-(2,2-dimethoxyethyl)-4-(2,4,6-trifluorobenzoyl)-1H-pyrrole-2-carboxamideYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF 5 mL solution of product obtained in step A (693 mg, 2.95 mmol) were added 4-(2,4,6-trifluoro-benzoyl)-1H-pyrrole-2-carboxylic acid (793 mg, 2.95 mmol), EDC (678 mg, 3.53 mmol), HOBt (541 mg, 3.53 mmol) and triethylamine (0.821 mL, 5.89 mmol). The reaction mixture was stirred overnight at room temperature. Resulting suspension was filtered and diluted with EtOAc. The organic layer was washed with sat. ammonium chloride aq., sat. sodium bicarbonate aq. and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give the title compound as oil (930 mg). LC/MS: m/z 487(M+H). 1H-NMR (500 MHz, CDCl3): δ 3.39 (s, 6H), 3.86 (br.s, 2H), 4.69 (d, 1H), 5.21 (s, 2H), 6.74 (t, 2H), 7.01 (br.s, 1H), 7.28 (s, 1H), 7.45 (dd, 2H), 7.65 (dd, 2H), 11.23 (s, 1H).

Workup

  1. customResulting suspension
  2. filtrationwas filtered
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed with sat. ammonium chloride aq., sat. sodium bicarbonate aq. and brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1b33a99e63344f74811671535eaf5dbd
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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