1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10226253, compound

HRID 2183822Notes

Reaction equation

HRID 2183822 reaction equation
[NH:1]([C:8]1[N:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([S:19][CH2:20][C:21]([OH:23])=O)[N:13]=[C:12]([CH3:24])[CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=N[CH2:36][CH2:37][CH2:38][N:39](C)C.C1C=CC2N(O)N=NC=2C=1.C1(N)CC1>C(Cl)Cl>[NH:1]([C:8]1[N:9]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[C:14]([S:19][CH2:20][C:21]([NH:39][CH:38]1[CH2:36][CH2:37]1)=[O:23])[N:13]=[C:12]([CH3:24])[CH:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 21948170HCID 21948170, compound

Product 1

HCID 10226253HCID 10226253, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of [(2-anilino-7-methyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridin-5-yl)sulfanyl]acetic acid (20 mg, 0.05 mmol), EDCI (18 mg, 0.10 mmol), HOBT (13 mg, 0.10 mmol) and cyclopropylamine (0.004 mL, 0.06 mmol) in CH2Cl2 (5 mL) was added TEA (0.02 mL, 0.14 mmol). The reaction solution was stirred at room temperature for 24 h before the mixture was diluted with CH2Cl2, washed with 0.5N HCl, saturated aqueous NaHCO3, brine and dried over Na2SO4. Solvents were removed in vacuo and the residue was purified by reverse-phase preparative HPLC (10% CH3CN in water with 0.1% TFA to 95% CH3CN in water, 10 mL/min, 10 min) to provide 2-[(2-anilino-7-methyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridin-5-yl)sulfanyl]-N-cyclopropylacetaide (13 mg, 59%): LCMS RT: 2.55 min, MH+: 457.1.

Workup

  1. washwashed with 0.5N HCl, saturated aqueous NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customSolvents were removed in vacuo
  4. customthe residue was purified by reverse-phase preparative HPLC (10% CH3CN in water with 0.1% TFA to 95% CH3CN in water, 10 mL/min, 10 min)
  5. customto provide 2-[(2-anilino-7-methyl-4-oxo-1-phenyl-1,4-dihydro-1,6-naphthyridin-5-yl)sulfanyl]-N-cyclopropylacetaide (13 mg, 59%)

Sources & evidence

ORD record
ord-8e3b306e0a6941d187a95c7136ec0437
Source dataset
uspto-grants-2005_05
Patent number
US06900205B2

Reaction notes

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