Acetic Acid → [3-(5-methyl-4-oxo-4,5-dihydro-3H-1,3,5,6-tetraaza-cyclopenta[a]naphthalen-2-yl)-cyclohexyl]-carbamic acid benzyl ester

HRID 2244813Notes

Reaction equation

HRID 2244813 reaction equation
[CH2:1]([O:8][C:9](=[O:33])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17](=O)[NH:18][C:19]2[C:20](=[O:31])[N:21]([CH3:30])[C:22]3[C:27]([C:28]=2[NH2:29])=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>>[CH2:1]([O:8][C:9](=[O:33])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[NH:18][C:19]3[C:20](=[O:31])[N:21]([CH3:30])[C:22]4[C:27](=[CH:26][CH:25]=[CH:24][N:23]=4)[C:28]=3[N:29]=2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 45123295[3-(4-Amino-1-methyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester

Product 1

HCID 58788434[3-(5-methyl-4-oxo-4,5-dihydro-3H-1,3,5,6-tetraaza-cyclopenta[a]naphthalen-2-yl)-cyclohexyl]-carbamic acid benzyl esterYield 85.5%

Conditions

Temperature
120 °C

Procedure

[3-(4-Amino-1-methyl-2-oxo-1,2-dihydro-[1,8]naphthyridin-3-ylcarbamoyl)-cyclohexyl]-carbamic acid benzyl ester (55 mg, 0.122 mmol) was dissolved in glacial acetic acid (1.32 g, 22.02 mmol) and heated at 120° C. for 15 h. After cooing to room temperature, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography, eluting with 2% MeOH in CH2Cl2 to give 45 mg (85%) of [3-(5-methyl-4-oxo-4,5-dihydro-3H-1,3,5,6-tetraaza-cyclopenta[a]naphthalen-2-yl)-cyclohexyl]-carbamic acid benzyl ester as a white solid. 1H-NMR (CDCl3): δ 8.61 (m, 2H), 7.33 (m, 7H), 5.18 (m, 2H), 4.27 (m, 1H), 4.0 (s, 3H), 3.81 (m, 1H), 3.44 (m, 1H), 2.52 (m, 3H), 2.28 (m, 1H), 2.12 (m, 1H), 1.8 (m, 1H), 1.79 (m, 3H), 1.31 (m, 1H). MS: calculated for C24H25N5O3+H 432.2; found: 432.0.

Workup

  1. customAfter cooing to room temperature
  2. customthe solvent was removed under reduced pressure
  3. customthe crude product was purified by flash chromatography
  4. washeluting with 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-ebf787d32c664420b3aadc059225d684
Source dataset
uspto-grants-2010_03
Patent number
US07678909B1

Reaction notes

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