1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21948200, compound

HRID 1063557Notes

Reaction equation

HRID 1063557 reaction equation
N([C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[N:15]=[C:14]([C:24]([OH:26])=O)[CH:13]=[C:12]([CH3:27])[C:11]=2[C:10](=[O:28])[CH:9]=1)C1C=CC=CC=1.Cl.[CH3:30][NH:31][O:32][CH3:33].[CH:34]1[CH:35]=[CH:36][C:37]2N(O)N=[N:40][C:38]=2[CH:39]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[NH:17]([C:8]1[N:40]([C:38]2[CH:39]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:16]2[N:15]=[C:14]([C:24]([N:31]([O:32][CH3:33])[CH3:30])=[O:26])[CH:13]=[C:12]([CH3:27])[C:11]=2[C:10](=[O:28])[CH:9]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 21948162HCID 21948162, compound

Product 1

HCID 21948200HCID 21948200, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-anilino-4-methyl-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxylic acid (50 mg, 0.14 mmol), N,O-dimethylhydroxylamine hydrochloride (39 mg, 0.40 mmol), HOBT (28 mg, 0.21 mmol), EDCI (40 mg, 0.21 mmol) were dissolved in CH2Cl2 (3 mL). To this solution was added TEA (78 uL, 0.56 mmol). The reaction was stirred for 1 h and was diluted with CH2Cl2, washed with 0.5N HCl, saturated NaHCO3, and brine. The organic layer was collected, dried over Na2SO4, and concentrated in vacuo. The solid obtained was triturated with Et2O and dried to give 7-anilino-N-methoxy-N,4-dimethyl-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridine-2-carboxamide as a light yellow solid (34 mg, 59%): LCMS RT: 2.28 min, MH+: 415.2. This transformation can also be accomplished by coupling the appropriate amine with the corresponding acid chloride.

Workup

  1. washwashed with 0.5N HCl, saturated NaHCO3, and brine
  2. customThe organic layer was collected
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe solid obtained
  6. customwas triturated with Et2O
  7. customdried

Sources & evidence

ORD record
ord-ddb3c154bb8e49bdafcefee0d3f9553d
Source dataset
uspto-grants-2005_11
Patent number
US06964971B2

Reaction notes

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