1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57500703, compound

HRID 1919690Notes

Reaction equation

HRID 1919690 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2=[CH:12][CH:13]=[CH:14][C:15]([C:16]([OH:18])=O)=[C:4]2[NH:3]1.C1C=CC2N(O)N=[N:25]C=2C=1.[NH4+].[Cl-].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN1C(=O)CCC1.[Cl-].[Na+].O.O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[C:5]2=[CH:12][CH:13]=[CH:14][C:15]([C:16]([NH2:25])=[O:18])=[C:4]2[NH:3]1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57500702HCID 57500702, compound

Product 1

HCID 57500703HCID 57500703, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxylic acid (1.0 eq, 1.91 g, 7.96 mmol) was mixed with HOBt.H2O (2.0 eq, 2.15 g, 15.91 mmol) and NH4Cl (8.0 eq, 3.41 g, 63.6 mmol) in NMP (30 ml). DIEA (4.0 eq, 5.5 ml, 31.57 mmol) and EDCI (2.0 eq, 3.05 g, 15.91 mmol) was added and the mixture was stirred in a closed vessel at 80° C. for 2.5 hours. Water and brine were added. The solid was filtered, washed with water, washed with methanol and dried in a vacuum oven. 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxamide was isolated as an off-white solid (1.81 g, 96% yield). LCMS (ES): m/z 240 [M+1]+.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. washwashed with methanol
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-dbd1420cbd754e6896743745a08e8cc4
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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