1-Hydroxybenzotriazole → HCID 66571400, compound

HRID 83635Notes

Reaction equation

HRID 83635 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=N[CH2:35][CH2:36][CH2:37][N:38](C)C)C.N1(O)[C:45]2[CH:46]=C[CH:48]=[CH:49][C:44]=2N=N1.C(N([CH:57]([CH3:59])[CH3:58])C(C)C)C>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:38][CH2:37][CH2:36][C:35]3[CH:48]=[CH:49][C:44]([CH:57]([CH3:58])[CH3:59])=[CH:45][CH:46]=3)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:27][CH:28]=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 66571400HCID 66571400, 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 (72.5 mg, 0.378 mmol), and 1H-benzo[d][1,2,3]triazol-1-ol (51.1 mg, 0.378 mmol) were dissolved in 2.0 mL of DCM and stirred for 10 minutes before the addition of a 2-(4-isopropylphenyl)ethanamine, HCl (75 mg, 0.378 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.132 mL, 0.756 mmol) as a 1.0 mL DCM solution. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The organic layer was washed with 1N HCl, saturated sodium bicarbonate solution, and finally saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material purified using silica gel chromatography 0-60% ethyl acetate/hexanes. (Yield: 50 mg, white solid) 1H-NMR (500 MHz, DMSO-d6) 7.88, 7.62, 7.55, 7.34, 7.22, 7.18-7.06, 6.71, 5.49, 4.40, 3.97, 3.24, 3.13-2.73, 2.66, 2.40-2.29, 1.79-1.23, 1.16

Workup

  1. washThe organic layer was washed with 1N HCl, saturated sodium bicarbonate solution, and finally saturated sodium chloride solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material purified

Sources & evidence

ORD record
ord-ad0ab93bdd7047648f60dce817b11468
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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