Ethylamine → HCID 25181984, compound

HRID 1697095Notes

Reaction equation

HRID 1697095 reaction equation
[CH3:1][O:2][C:3]([C:5]1N(C2C=CC=CC=2)[C:7]2[C:12]([C:13](=[O:25])[C:14]=1[CH2:15][C:16]1[CH:17]=[N:18][C:19]([C:22](O)=[O:23])=[CH:20][CH:21]=1)=[CH:11][CH:10]=[C:9]([CH3:26])[N:8]=2)=[O:4].F[P-](F)(F)(F)(F)F.[N:40]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1.[CH2:60]([NH2:62])[CH3:61].CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:40]([C:44]2[CH:43]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:7]2[C:12]([C:13](=[O:25])[C:14]=1[CH2:15][C:16]1[CH:17]=[N:18][C:19]([C:22](=[O:23])[NH:62][CH2:60][CH3:61])=[CH:20][CH:21]=1)=[CH:11][CH:10]=[C:9]([CH3:26])[N:8]=2)=[O:4]

Participants

7

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66816229HCID 66816229, compound

Product 1

HCID 25181984HCID 25181984, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-(6-carboxy-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]-naphthyridine-2-carboxylic acid methyl ester (0.11 g) in DCM was added BOP (0.14 g), followed by ethylamine (0.016 g) and Hunig's Base (0.06 mL), and the mixture stirred at RT overnight. The product was taken up in EtOAc and H2O, washed with NaHCO3 (aq), and dried over MgSO4, then filtered, concentrated, and purified by prep TLC using 100% EtOAc, to provide 3-(6-ethylcarbamoyl-pyridin-3-ylmethyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro[1,8]-naphthyridine-2-carboxylic acid methyl ester (compound 101) as an off-white solid. M+H=457.

Workup

  1. washH2O, washed with NaHCO3 (aq)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by prep TLC

Sources & evidence

ORD record
ord-b68164de59224e4598d9cea902b1bd17
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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