1,2-Dichloroethane → HCID 68159059, compound

HRID 243260Notes

Reaction equation

HRID 243260 reaction equation
[F:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[C:4]([NH:9][CH3:10])[C:5]([NH2:8])=[CH:6][CH:7]=1.[NH:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:18]([C:20](O)=O)[CH3:19].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[C:26]([O:25][C:23](=[O:24])[NH:17][C@H:18]([C:20]1[N:9]([CH3:10])[C:4]2[C:3]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[C:2]([F:1])[CH:7]=[CH:6][C:5]=2[N:8]=1)[CH3:19])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 68156998HCID 68156998, compound

Product 1

HCID 68159059HCID 68159059, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-fluoro-N2-methyl-3-pyridin-2-yl-benzene-1,2-diamine (0.75 g, 3.44 mmol), Boc-Ala (0.72 g, 3.78 mmol), HOAt (0.52 g, 3.78 mmol) in DCM (10 mL) was cooled to 0° C. EDC (0.73 g, 3.78 mmol) was added portion wise and the resulting mixture was stirred for 1 h. The mixture was diluted with DCM (20 mL) and the organic layer was washed with citric acid, brine, dried (MgSO4) and evaporated. The resulting residue was purified by chromatography (Si—PPC, gradient 0-50% EtOAc/cyclohexane) to afford the title compound as a white solid (0.3 g, 24%). LCMS (Method J): RT 2.42 min [M+H]+ 371

Workup

  1. washthe organic layer was washed with citric acid, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe resulting residue was purified by chromatography (Si—PPC, gradient 0-50% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-6a585128c9114095b3fb2ce61ea1b4fe
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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