3-Aminoquinoline → HCID 70207200, compound

HRID 1067061Notes

Reaction equation

HRID 1067061 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:32]([OH:34])=[O:33])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:35][C:36]1C=NC2C(C=1)=CC=CC=2.C(N(C(C)C)CC)(C)C.P(Cl)(Cl)(Cl)=O>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.C(Cl)Cl>[N:35]1[C:12]2[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[C:9]([C:17]([NH2:19])=[O:18])[CH:36]=1.[C:1]([NH:8][C@H:9]([C:17]([NH:19][C@H:20]([C:32]([OH:34])=[O:33])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

8

Reactant 4

HCID 113753-AminoquinolineHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 70207201HCID 70207201, compound

Product 1

HCID 70207200HCID 70207200, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A cold solution (0° C.) of N-Boc-phenylalanyl-Nδ-Boc-ornithine (0.2 g, 0.4 mmol), 3-aminoquinoline (0.082 g, 0.57 mmol), diisopropylethylamine (0.103 mg, 0.8 mmol), 4-(dimethylamino)pyridine (5 mg, 0.04 mmol), and methylene chloride (3 mL) was treated dropwise with phosphorus oxychloride (0.5 mmol). The reaction was stirred at 0° C. for 1 hr and ethyl acetate (20 mL) was added. The organic layer was washed with water (2×20 mL), 1N hydrochloric acid (2×10 mL), saturated sodium bicarbonate (2×10 mL) and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate adsorbed onto 100 mg of silica gel and applied to a column prepacked with silica gel. The column was eluted with ethyl acetate/hexane (70:30, v:v) to afford titled compound (51 mg) as an oil: 1H NMR (400 MHz, CDCl3) δ1.42-1.55 (18H), 1.6-1.8 (1H), 2.0-2.1 (1H), 3.1-3.2 (4H), 3.3-3.4 (1H), 4.19-4.21 (1H), 4.70-4.80 (1H), 5.0-5.15 (1H), 7.21-7.29 (5H), 7.53-7.55 (1H), 7.63-7.65 (1H), 7.79-7.81 (1H), 8.05-8.07 (1H), 8.74 (1H), 8.94 (1H); mass spectrum (relative intensity) m/e 606 (100, M+1).

Workup

  1. washThe organic layer was washed with water (2×20 mL), 1N hydrochloric acid (2×10 mL), saturated sodium bicarbonate (2×10 mL) and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. washThe column was eluted with ethyl acetate/hexane (70:30, v:v)

Sources & evidence

ORD record
ord-8873debd23854708a5fdec05d5a12715
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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