Triethylamine → HCID 66885285, compound

HRID 1925828Notes

Reaction equation

HRID 1925828 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:18]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[Cl:27])=[C:17]([F:28])[C:8]2[N:9]=[CH:10][N:11]([CH2:12][CH2:13][C:14](O)=[O:15])[C:7]=2[CH:6]=1)=[O:4].[CH:29]1[CH:30]=CC2N(O)N=[N:35][C:33]=2[CH:34]=1.O.CCN(CC)CC.N1CCCC1.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:18]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[Cl:27])=[C:17]([F:28])[C:8]2[N:9]=[CH:10][N:11]([CH2:12][CH2:13][C:14](=[O:15])[N:35]3[CH2:30][CH2:29][CH2:34][CH2:33]3)[C:7]=2[CH:6]=1)=[O:4]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 27960291-Hydroxybenzotriazole hydrateHCID 66886231HCID 66886231, compound

Product 1

HCID 66885285HCID 66885285, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution of 6-(4-bromo-2-chloro-phenylamino)-3-(2-carboxy-ethyl)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester (60 mg, 0.13 mmol) in DMF (1.8 mL) is added HOBt-H2O (24 mg, 0.16 mmol), Et3N (0.043 mL, 0.31 mmol), pyrrolidine (0.011 mL, 0.13 mmol), and EDCI (34 mg, 0.18 mmol) at room temperature. The resulting yellow solution is stirred 16 hours at room temperature. The reaction mixture is diluted with EtOAc and water, washed with sat'd aqueous NH4Cl, brine, sat'd aqueous NaHCO3, and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo to give a crude material which is purified by flash chromatography (3% MeOH in CH2Cl2) to afford 45 mg (67%) of the desired product: MS APCI (+) m/z 523, 525 (M+, Br pattern) detected.

Workup

  1. washwashed with sat'd aqueous NH4Cl, brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude material which
  6. customis purified by flash chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-07b355d41269499d898abc3bbdd7462f
Source dataset
uspto-grants-2012_05
Patent number
US08178693B2

Reaction notes

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