Pyridine → HCID 59199444, compound

HRID 2089535Notes

Reaction equation

HRID 2089535 reaction equation
[CH:1]([O:4][C:5]([C:7]1[N:8]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH2:22])[CH:20]=3)[CH2:15][CH2:14][CH2:13]2)[CH:9]=[N:10][CH:11]=1)=[O:6])([CH3:3])[CH3:2].N1C=CC=CC=1.[C:29](Cl)(=[O:31])[CH3:30]>ClCCl>[CH:1]([O:4][C:5]([C:7]1[N:8]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([NH:22][C:29](=[O:31])[CH3:30])[CH:20]=3)[CH2:15][CH2:14][CH2:13]2)[CH:9]=[N:10][CH:11]=1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 59199337HCID 59199337, compound

Product 1

HCID 59199444HCID 59199444, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(7-amino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester (0.180 g, 0.602 mmol) and pyridine (0.052 g, 0.662 mmol) in dichloromethane (2 mL) is added acetyl chloride (0.052 g, 0.662 mmol) at 0° C. and the reaction is stirred for 2.5 hours. The solution is then washed with 10% aqueous HCl and water and the combined aqueous phases are extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, filtered, and concentrated to give a residue, which is purified by silica gel chromatography (dichloromethane-methanol mixtures) to give 3-(7-acetylamino-1,2,3,4-tetrahydro-naphthalen-1-yl)-3H-imidazole-4-carboxylic acid isopropyl ester; MS: (ESI) m/z 342.2 (M+H)+; 1H NMR (400 MHz, MeOD) δ ppm 1.39 (d, J=6.3 Hz, 3 H), 1.40 (d, J=6.3 Hz, 3 H), 1.78-1.92 (m, 2 H), 2.08 (s, 3 H), 2.16-2.31 (m, 2 H), 2.81-2.89 (m, 1 H), 2.98 (dt, J=16.9, 6.1 Hz, 1 H), 5.25 (sept, J=6.3 Hz, 1 H), 6.32 (t, J=5.4 Hz, 1 H), 7.17 (br. s, 1 H), 7.22 (d, J=8.3 Hz, 1 H), 7.43 (s, 1 H), 7.50 (dd, J=8.3, 2.1 Hz, 1 H), 7.74 (d, J=1.0 Hz, 1 H).

Workup

  1. washThe solution is then washed with 10% aqueous HCl and water
  2. extractionthe combined aqueous phases are extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue, which
  7. customis purified by silica gel chromatography (dichloromethane-methanol mixtures)

Sources & evidence

ORD record
ord-deea325008d349f1931335c7b987aaaa
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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