1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58869824, compound

HRID 2402280Notes

Reaction equation

HRID 2402280 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[CH2:18][CH2:19][C:20](NC1SC=CN=1)=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:49][O:50][C:51](=[O:59])[C:52]1[CH:57]=[CH:56][C:55]([NH2:58])=[N:54][CH:53]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:49][O:50][C:51](=[O:59])[C:52]1[CH:57]=[CH:56][C:55]([NH:58][C:20](=[O:21])[CH2:19][CH2:18][CH:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16](=[O:17])[N:8]2[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:54][CH:53]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 737487Methyl 6-aminonicotinateHCID 58869823HCID 58869823, compound

Product 1

HCID 58869824HCID 58869824, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 1, Part E (200 mg, 0.68 mmol) was dissolved in 5 mL DMF. HOBt (312 mg, 2.04 mmol) and EDCI (340 mg, 2.04 mmol) were added and the mixture was stirred at room temperature for 0.5 h. 6-Aminonicotinic acid methyl ester (156 mg, 1.02 mmol) was added and the mixture was stirred for 16 h. The mixture was poured into 100 mL sat'd NaHCO3 and extracted with EtOAc. The combined organic phase was washed with water and brine, then dried (Na2SO4), filtered and evaporated. The product was purified by silica gel chromatography (10 mg, 3%). 1H NMR (300 MHz, acetone-d6) δ 9.64 (br s, 1H), 8.78 (s, 1H), 8.26 (s, 2H), 7.78 (d, J=7 Hz, 1H), 7.62 (m, 2H), 7.51 (m, 1H), 7.34 (m, 5H), 5.25 (d, J=15 Hz, 1H), 4.64 (m, 1H), 4.39 (d, J=15 Hz, 1H), 3.89 (s, 3H), 2.51 (m, 2H), 2.21 (m, 1H), 2.01 (m, 1H). MS: m/z (MH+) 430.

Workup

  1. stirringthe mixture was stirred for 16 h
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by silica gel chromatography (10 mg, 3%)

Sources & evidence

ORD record
ord-91e9b372523a4ccb9c237e33da06f281
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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