1,2-Dichloroethane → HCID 18433581, compound

HRID 2306224Notes

Reaction equation

HRID 2306224 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]([CH2:13][CH2:14][C:15]([O-:17])=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:20])#[N:2].[Li+].Cl.CN[O:25][CH3:26].C1C=CC2N(O)N=[N:33][C:31]=2C=1.C(Cl)CCl.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]([CH2:13][CH2:14][C:15]([NH:33][CH2:31][O:25][CH3:26])=[O:17])=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:20])#[N:2]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 23711715HCID 23711715, compound

Product 1

HCID 18433581HCID 18433581, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of lithium 3-[1-(4-cyano-3-fluorobenzyl)-1H-imidazol-5-yl]propionate, as described in Example 34, Step E, (500 mg, 1.79 mmol), N,O-dimethylhydroxylamine hydrochloride (874 mg, 8.96 mmol), HOBT (270 mg, 2.00 mmol), EDC (418 mg, 2.18 mmol), and N,N-diisopropylethylamine (1.87 mL, 10.74 mmol) was stirred in DMF (5 mL) at ambient temperature for 18 hours. EtOAc (50 mL) was added, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with a gradient of CHCL3—1% MeOH—0.1% NH4OH to CHCl3—4% MeOH—0.4% NH4OH to yield the titled product.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica
  4. washeluting with a gradient of CHCL3—1% MeOH—0.1% NH4OH to CHCl3—4% MeOH—0.4% NH4OH

Sources & evidence

ORD record
ord-2f13cc68ea0c4a35bfc3eb74dda6adf8
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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