1,2-Dichloroethane → HCID 58286517, compound

HRID 2098457Notes

Reaction equation

HRID 2098457 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24](O)=[O:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:25]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2332402-Benzimidazolecarboxylic acidHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 58286517HCID 58286517, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1,1-dimethylethyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (18.3 g, 92.5 mmol), 1H-benzimidazole-2-carboxylic acid, (15.0 g, 92.5 mmol), EDC (21.3 g, 111 mmol), HOBt (2.5 g, 18.5 mmol), NMM (28 g, 277.5 mmol) in CH2Cl2 (250 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2 then washed with sat. NaHCO3 (200 mL) and brine (200 mL). The solution was dried over anhydrous Na2SO4 and concentrated to give a crude product which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate: 2/1) to give the title compound (20 g) as a white solid. LCMS (m/z): 343.2 (M+H).

Workup

  1. washthen washed with sat. NaHCO3 (200 mL) and brine (200 mL)
  2. dry with materialThe solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give a crude product which
  5. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate: 2/1)

Sources & evidence

ORD record
ord-ae0677e762b04f509b11776a5f3bcacf
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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