1,2-Dichloroethane → HCID 66571401, compound

HRID 83632Notes

Reaction equation

HRID 83632 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=O)[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.ON1C2C=CC=CC=2N=N1.C(Cl)CCl.[O:43]1[C:47]2=[CH:48][N:49]=[CH:50][CH:51]=[C:46]2[CH:45]([CH2:52][NH2:53])[CH2:44]1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([NH:53][CH2:52][CH:45]3[C:46]4[C:47](=[CH:48][N:49]=[CH:50][CH:51]=4)[O:43][CH2:44]3)=[O:26])[CH2:20][CH2:19]2)=[O:17])=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 45079788HCID 45079788, compoundHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 66571401HCID 66571401, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (317 mg, 0.799 mmol), 1-hydroxybenzotriazole (135 mg, 0.999 mmol), and EDC (191 mg, 0.999 mmol) were dissolved in 2.0 mL of DCM. The reaction was allowed to stir at room temperature for 10 minutes before adding (2,3-dihydrofuro[2,3-c]pyridin-3-yl)methanamine (100 mg, 0.666 mmol) as a DCM solution and Hunig'sBase (0.174 mL, 0.999 mmol). The reaction was allowed to stir at room temperature overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride solution. It was dried over magnesium sulfate, filtered and concentrated. The crude material was triturated in ethyl acetate, filtered and concentrated to obtain white solid. (Yield: 176 mg, white solid) 1H-NMR (500 MHz, DMSO-d6) 8.13-8.04, 7.63, 7.55, 7.37-7.28, 7.22, 7.13-7.02, 6.72, 5.47, 4.59, 4.47-4.28, 4.13-3.85, 3.73-3.62, 3.17, 3.07-2.76, 2.41-2.31, 1.79-1.20

Workup

  1. stirringto stir at room temperature overnight
  2. washThe organic layer was washed with saturated sodium bicarbonate and saturated sodium chloride solution
  3. dry with materialIt was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was triturated in ethyl acetate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain white solid

Sources & evidence

ORD record
ord-ba55fbb7e29a43f3b6cce3a2f153de1d
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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