1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178467958, compound

HRID 578982Notes

Reaction equation

HRID 578982 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:5][CH:4]=1)#[N:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.[CH2:54]([O:56][CH2:57][CH2:58][NH2:59])[CH3:55]>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([NH:59][CH2:58][CH2:57][O:56][CH2:54][CH3:55])=[O:20])=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:7][CH:8]=1)#[N:2]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66970EthoxyethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178509615HCID 178509615, compound

Product 1

HCID 178467958HCID 178467958, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Combined 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (100 mg, 0.327 mmol), EDCI (94.0 mg, 0.490 mmol), and HOBT (66.2 mg, 0.490 mmol) in DMF (2.5 mL) and added N,N-diisopropyl ethylamine (227 μL, 1.306 mmol). Then 2-ethoxyethanamine (43.7 mg, 0.490 mmol) was added and the reaction allowed to stir at room temperature for 16 hours. The reaction mixture was then diluted with water (3.5 mL) and acidified to an approximate pH=4 to give a solid which was collected by filtration, washed with water, MeOH, and diethyl ether to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.04 (t, J=6.95 Hz, 3 H) 3.33-3.41 (m, 4 H) 3.41-3.48 (m, 2 H) 7.70 (d, J=8.34 Hz, 2 H) 8.06 (d, J=7.07 Hz, 2 H) 8.26-8.49 (m, 2 H) 8.58 (br. s., 1 H) 8.71 (t, J=5.18 Hz, 1 H) 8.77-8.93 (m, 1 H) 12.95-13.90 (m, 1 H). MS m/z [M+H]+ 378.1.

Workup

  1. customto give a solid which
  2. filtrationwas collected by filtration
  3. washwashed with water, MeOH, and diethyl ether

Sources & evidence

ORD record
ord-6f628a5dd94e47919381e716f766d911
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

Loading…