1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57402606, compound

HRID 1919686Notes

Reaction equation

HRID 1919686 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[C:12]3=[CH:19][CH:20]=[CH:21][C:22]([C:23]([OH:25])=O)=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C1C=CC2N(O)N=[N:32]C=2C=1.[Cl-].[NH4+].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN1C(=O)CCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[C:12]3=[CH:19][CH:20]=[CH:21][C:22]([C:23]([NH2:32])=[O:25])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 50941395HCID 50941395, compound

Product 1

HCID 57402606HCID 57402606, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carboxylic acid (20 mg) was reacted in NMP (0.4 ml) with HOBt.H2O (40 mg), ammonium chloride (40 mg), DIEA (100 ul) and EDCI (50 mg) at 70° C. for 1 hour. Water was added and the precipitate filtered and dried. After trituration in methanol and filtration, 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-7-carboxamide was isolated as a solid (8 mg). LCMS (ES): >95% pure, m/z 349 [M+1]+.

Workup

  1. filtrationthe precipitate filtered
  2. customdried
  3. filtrationAfter trituration in methanol and filtration

Sources & evidence

ORD record
ord-ced31c85735247f5a21648c56be01cb1
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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