1,2-Dichloroethane → HCID 67072439, compound

HRID 2098461Notes

Reaction equation

HRID 2098461 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:17][C@@H:16]2[CH2:18][C@H:13]1[CH2:14][N:15]2[C:19](=[O:26])[C@@H:20]([NH2:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:11].[CH3:27][C:28]1[CH:36]=[C:35]2[C:31]([CH:32]=[C:33]([C:37](O)=[O:38])[NH:34]2)=[CH:30][CH:29]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:17][C@@H:16]2[CH2:18][C@H:13]1[CH2:14][N:15]2[C:19]([C@@H:20]([NH:25][C:37]([C:33]1[NH:34][C:35]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[C:28]([CH3:27])[CH:36]=2)=[O:38])[C:21]([CH3:22])([CH3:23])[CH3:24])=[O:26])=[O:11]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 31633966-Methyl-1H-indole-2-carboxylic acidHCID 58286598HCID 58286598, compound

Product 1

HCID 67072439HCID 67072439, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (2S)-1-[(1S,4S)-5-(1H-benzimidazol-2-ylcarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]-3,3-dimethyl-1-oxo-2-butanamine (120 mg, 0.34 mmol), 6-methyl-1H-indole-2-carboxylic acid (60 mg, 0.34 mmol), EDC (78 mg, 0.41 mmol), HOBt (9 mg, 0.068 mmol), NMM (103 mg, 1.02 mmol) in CH2Cl2 (2 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2 then washed with sat. NaHCO3 (20 mL) and brine (20 mL). The solution was dried over anhydrous Na2SO4 and concentrated to give the crude product, which was purified by reverse phase HPLC: 50-80% ACN/Water (0.1% TFA). Concentration of the fractions containing product afforded the title compound (105 mg) as a white solid. LCMS (m/z): 513.1 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 0.90-1.10 (m, 9H), 1.75-2.20 (m, 2H), 2.30-2.40 (m, 3H), 3.45-3.95 (m, 3H), 4.00-5.25 m, 4H), 6.20-6.75 (m, 1H), 6.80-7.70 (m, 9H), 9.30-9.70 (m, 1H)

Workup

  1. washthen washed with sat. NaHCO3 (20 mL) and brine (20 mL)
  2. dry with materialThe solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by reverse phase HPLC
  6. additionConcentration of the fractions containing product

Sources & evidence

ORD record
ord-902f6497c96a446c9569eb7924b69e51
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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