1,2-Dichloroethane → HCID 178517740, compound

HRID 1012154Notes

Reaction equation

HRID 1012154 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[NH:9][C:8]([C:13]2[C:17]([NH:18][C:19](=[O:28])[C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[F:27])=[CH:16][NH:15][N:14]=2)(C(O)=O)[NH:7][CH:6]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN([CH:46]=[O:47])C>ClCCl>[F:27][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([F:26])[C:20]=1[C:19]([NH:18][C:17]1[C:13]([C:8]2[NH:9][C:5]3[CH2:4][CH2:3][CH2:2][NH:1][C:46](=[O:47])[C:6]=3[N:7]=2)=[N:14][NH:15][CH:16]=1)=[O:28]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 178510929HCID 178510929, compound

Product 1

HCID 178517740HCID 178517740, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(3-amino-propyl)-2-[4-(2,6-difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-imidazole carboxylic acid (200 mg, 0.51 mmoles) in DMF (10 ml) and dichloromethane (10 ml) was added EDC (118 mg, 0.62 mmoles), HOBt (84 mg, 0.62 mmoles) and NEM (260 μl, 2.04 mmoles). The solution was stirred at ambient temperature for 48 hours and then partitioned between EtOAc and water. The organic portion was dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by flash column chromatography [silica, 3% MeOH in DCM to 5% to 10%] to give 2,6-difluoro-N-[3-(4-oxo-1,4,5,6,7,8-hexahydro-1,3,5-triaza-azulen-2-yl)-1H-pyrazol-4-yl]-benzamide as a pale yellow solid (10 mg, 13%). (LC/MS: Rt 1.93, [M+H]+ 372.99).

Workup

  1. custompartitioned between EtOAc and water
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography [silica, 3% MeOH in DCM to 5% to 10%]

Sources & evidence

ORD record
ord-e22ecfb8a0ef47859eda3dfc39028ca0
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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