Triethylamine → HCID 131733288, compound

HRID 1748395Notes

Reaction equation

HRID 1748395 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17](Cl)=[O:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1.[NH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]([NH:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:18])[CH:13]=[N:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 90417622HCID 90417622, compound

Product 1

HCID 131733288HCID 131733288, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-((3-chlorobenzyl)oxy)quinoline-3-carbonyl chloride in THF (1.5 mL) was added tert-butyl (2-aminoethyl)carbamate (38 mg, 0.23 mmol) and triethylamine (0.044 mL, 0.32 mmol). The reaction was stirred for 14 h. The crude reaction was loaded directly onto a column and purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound as a white solid (44 mg, 60%). 1H NMR (400 MHz, CDCl3) δ 9.31-9.20 (m, 1H), 8.61-8.51 (m, 1H), 7.80 (d, J=9.0 Hz, 1H), 7.68-7.60 (m, 1H), 7.49 (s, 2H), 7.40-7.29 (m, 4H), 5.20 (s, 2H), 5.09-4.92 (m, 1H), 3.68-3.59 (m, 2H), 3.50-3.43 (m, 2H), 1.44 (s, 9H). [M+H]=456.3

Workup

  1. customThe crude reaction
  2. customwas loaded directly onto a column and purification (FCC, SiO2, 0-5%, MeOH/DCM)

Sources & evidence

ORD record
ord-bf31f34795164f0a8ab9e6342a49d22e
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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