1-Hydroxybenzotriazole → HCID 57385298, compound

HRID 83629Notes

Reaction equation

HRID 83629 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](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.Cl.C(N=C=NCCCN(C)C)C.[N:41]1(O)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2N=N1.C(N(C(C)C)C(C)C)C>O.C(OCC)(=O)C.C(Cl)Cl>[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]([NH:41][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:44]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 57385298HCID 57385298, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (97 mg, 0.504 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (68.1 mg, 0.504 mmol) were dissolved 2.0 mL of DCM. The reaction was stirred at room temperature for ten minutes before N-ethyl-N-isopropylpropan-2-amine (0.088 mL, 0.504 mmol) and aniline, HCl (65.3 mg, 0.504 mmol) as a 1.0 mL DCM solution was added. The reaction was allowed to stir at room temperature overnight. The reaction was diluted with water and ethyl acetate. The organic phase was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride. The organic phase was dried over magnesium sulfate, filtered and concentrated. The crude material was recrystallized with ether and ethyl acetate and filtered to obtain white solid as a product. (Yield: 77 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 9.89, 7.66-7.52, 7.37-7.18, 7.13-7.07, 7.02, 6.75, 5.51, 4.44, 4.03, 2.95, 2.64-2.55, 1.79, 1.47

Workup

  1. additionwas added
  2. washThe organic phase was washed with water, saturated sodium bicarbonate (twice), and saturated sodium chloride
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was recrystallized with ether and ethyl acetate
  7. filtrationfiltered
  8. customto obtain white solid as a product

Sources & evidence

ORD record
ord-1e359169442f41ed96c267ec0c28294f
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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