Triethylamine → HCID 18470601, compound

HRID 2228470Notes

Reaction equation

HRID 2228470 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[Cl:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=1[C:36]1[C:40]([C:41](Cl)=[O:42])=[C:39]([CH3:44])[O:38][N:37]=1>ClCCl.C(OCC)(=O)C.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:41]([C:40]1[C:36]([C:30]2[C:31]([F:35])=[CH:32][CH:33]=[CH:34][C:29]=2[Cl:28])=[N:37][O:38][C:39]=1[CH3:44])=[O:42])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 187201N-BOC-ethylenediamineHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride

Product 1

HCID 18470601HCID 18470601, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-t-butyloxycarbonyl-1,2-diaminoethane (355 mg, 2.22 mmol), dimethylaminopyridine (27 mg, 0.222 mmol), and triethylamine (247 mg, 2.44 mmol) were combined in 5 mL of dry dichloromethane. 3-(2-Chloro-6-fluorophenyl)-5-methylisoxazol-4-oyl chloride (607 mg, 2.22 mmol) was added in slowly. The reaction was stirred for 3 hours at room temperature under nitrogen. The reaction was diluted with ethyl acetate and water. The ethyl acetate was separated and washed three times each with 25 mL of 1N aqueous hydrochloric acid and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was treated with hexanes to crystallize 794 mg of the title compound. (90%). EA calculated for: C18H21N3O4ClF: C, 54.34; H, 5.32; N, 10.56. Found: C, 54.30; H, 5.36; N, 10.44. MS(IS) m/z 398 (M+).

Workup

  1. customThe ethyl acetate was separated
  2. washwashed three times each with 25 mL of 1N aqueous hydrochloric acid and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionThe residue was treated with hexanes
  7. customto crystallize 794 mg of the title compound

Sources & evidence

ORD record
ord-9a961021d8e34c889a04ff50870959e5
Source dataset
uspto-grants-2002_07
Patent number
US06417193B1

Reaction notes

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