2,9-Dimethyl-1,10-phenanthroline → 2-Amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester

HRID 1984604Notes

Reaction equation

HRID 1984604 reaction equation
CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.[CH2:17]([O:22][C:23](=[O:32])[C:24]1[C:29](I)=[CH:28][N:27]=[C:26]([NH2:31])[CH:25]=1)[CH2:18][CH2:19][CH2:20][CH3:21].[N:33]1([S:39]([C:42]2[CH:47]=[CH:46][C:45]([SH:48])=[CH:44][CH:43]=2)(=[O:41])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.[Cu](I)I>[CH2:17]([O:22][C:23](=[O:32])[C:24]1[C:29]([S:48][C:45]2[CH:44]=[CH:43][C:42]([S:39]([N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)(=[O:40])=[O:41])=[CH:47][CH:46]=2)=[CH:28][N:27]=[C:26]([NH2:31])[CH:25]=1)[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

7

Reactant 4

HCID 652372,9-Dimethyl-1,10-phenanthrolineHCID 23676156Sodium t-butoxideHCID 57718193HCID 57718193, compoundHCID 577182904-(N-piperidinylsulfonyl)thiophenol

Product 1

HCID 577182132-Amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl esterYield 56%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

Procedure

Copper iodide (26 mg, 0.14 mmol) and neocuproine (29 mg, 0.14 mmol) were added to a stirred mixture of 2-amino-5-iodo-isonicotinic acid pentyl ester (450 mg, 1.35 mmol), 4-(piperidine-1-sulfonyl)-benzenethiol (449 mg, 1.49 mmol) and sodium t-butoxide (195 mg, 2.025 mmol) in toluene (10 ml) and the reaction was heated to reflux overnight. The reaction was cooled to room temperature, solids filtered off through celite and the filtrate concentrated under reduced pressure onto silica. The residue was purified by flash column chromatography using ethyl acetate 2/3 hexane as eluent to afford 2-amino-5-[4-(piperidine-1-sulfonyl)-phenylsulfanyl]-isonicotinic acid pentyl ester as an orange solid (348 mg, 56%). 1H NMR (CDCl3): (1H, s, py); 7.51 (2H, d, Ar); 7.10 (2H, d, Ar); 6.80 (1H, s, py); 4.92 (2H, br s, NH2); 4.14 (2H, t, OCH2); 2.90 (4H, m, 2×CH2N pip); 1.53 (6H, m, OCH2CH2, 2×CH2 pip); 1.46 (2H, m, CH2 pip); 1.24 (4H, m, OCH2CH2CH2CH2CH3); 0.80 (3H, t, CH2CH3).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationsolids filtered off through celite
  4. concentrationthe filtrate concentrated under reduced pressure onto silica
  5. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-8e1046b6e9b44611a5aae62713ac15c6
Source dataset
uspto-grants-2009_06
Patent number
US07544702B2

Reaction notes

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