1,2-Dichloroethane → HCID 131723948, compound

HRID 1355591Notes

Reaction equation

HRID 1355591 reaction equation
[CH2:1]([S:5]([NH:8][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[NH2:15][C@H:16]([C:18]([OH:20])=O)[CH3:17].[CH2:21](Cl)CCl.O[N:26]1[C:30]2C=CC=CC=2N=N1.[N:35]1[C:40](C)=[CH:39][C:38](C)=[CH:37][C:36]=1[CH3:43]>C(#N)C>[CH2:1]([S:5]([NH:8][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])(=[O:6])=[O:7])[CH2:2][CH2:3][CH3:4].[C:30]([C:40]1[CH:39]=[CH:38][C:37]([CH2:36][NH:43][C:18](=[O:20])[C@H:16]([CH3:17])[NH2:15])=[CH:21][CH:35]=1)#[N:26]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 79532,4,6-TrimethylpyridineHCID 757711-HydroxybenzotriazoleHCID 87354904HCID 87354904, compound

Product 1

HCID 131723948HCID 131723948, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of compound 4 (150 mg, 0.51 mmol), 4-(aminomethyl)benzylnitrile (compound 6, 171 mg, 1.02 mmol), EDC (195 mg, 1.02 mmol), and N-hydroxybenzotriazole (78 mg, 0.51 mmol) in acetonitrile (5.1 ml) was stirred at ambient temperature for 10 minutes. 2,4,6-Collidine (0.34 ml, 2.54 mmol) was then added and the reaction mixture was stirred overnight at ambient temperature. The solvent was removed under reduced pressure and the resulting residue was resuspended in ethylacetate (100 ml) and 0.5M HCl (10 ml). The ethylacetate layer was washed with water followed by 0.5M HCl (10 ml), saturated sodium bicarbonate (2×10 ml) and brine (15 ml), then dried with sodium sulfate. The solvent was removed under reduced pressure to yield 237 mg product. The product eluted at 9.5 minutes by reverse phase (C18) HPLC at 0.11 trifluoroacetic acid in 5-75% aqueous acetonitrile over 20 minutes.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washThe ethylacetate layer was washed with water
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-38f9fd05fe11465a842754353da7fa80
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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