1-Hydroxybenzotriazole → HCID 71208829, compound

HRID 1887913Notes

Reaction equation

HRID 1887913 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:31])[C:7]([CH2:18][NH:19][C:20]([C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=3)=[O:21])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.N[CH2:33][C:34]([CH3:37])([OH:36])[CH3:35].O[N:39]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:31])[C:7]([CH2:18][N:19]([CH2:33][C:34]([OH:36])([CH3:37])[CH3:35])[C:20](=[O:21])[C:22]3[CH:23]=[CH:24][C:25]([C:26]([NH2:39])=[O:28])=[CH:29][CH:30]=3)=[CH:8][N:9]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71208481HCID 71208481, compound

Product 1

HCID 71208829HCID 71208829, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 4-((7-chloro-4-oxo-1-phenyl-1,4-dihydroquinolin-3-yl)methylcarbamoyl)benzoic acid (25.3 mg, 0.058 mmol), 1-amino-2-methylpropan-2-ol (5.21 mg, 0.058 mmol), 1-hydroxybenzotriazole (HOBT) (12.9 mg, 0.094 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) (18.1 mg, 0.094 mmol) in methylene chloride at 25° C. was treated with N,N-diisopropylethylamine (76.3 mg, 103 μL, 0.584 mmol). The reaction was stirred at 25° C. overnight. The reaction was diluted with methylene chloride (20 mL) and was washed with a saturated aqueous ammonium chloride solution (1×50 mL) and a saturated aqueous sodium bicarbonate solution (1×50 mL). The organics were dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (2% methanol/methylene chloride ramped to 6% methanol/methylene chloride) provided N-(7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinolin-3-ylmethyl)-N-(2-hydroxy-2-methyl-propyl)-terephthalamide (14.3 mg, 49%) 1H NMR (300 MHz, DMSO-d6) δ ppm 8.85 (t, J=5.27 Hz, 1H) 8.33 (t, J=6.12 Hz, 1H) 8.28 (d, J=8.67 Hz, 1H) 7.91 (s, 4H) 7.99 (s, 1H) 7.54-7.74 (m, 5H) 7.46 (dd, J=8.67, 1.88 Hz, 1H) 6.91 (d, J=1.70 Hz, 1H) 4.54 (s, 1H) 4.40 (d, J=5.46 Hz, 2H) 3.25 (d, J=6.03 Hz, 2H) 1.08-1.14 (m, 6H).

Workup

  1. washwas washed with a saturated aqueous ammonium chloride solution (1×50 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29497f170e5f4377a39c01b233bf0505
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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