Diisopropylethylamine → HCID 66813325, compound

HRID 1099599Notes

Reaction equation

HRID 1099599 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[N:11]([C:21]2[CH:26]=[CH:25][C:24]([S:27](=[O:30])(=[O:29])[NH2:28])=[CH:23][CH:22]=2)[N:10]=1.C(N(CC)C(C)C)(C)C>ClCCl>[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[N:11]([C:21]2[CH:26]=[CH:25][C:24]([S:27](=[O:29])(=[O:30])[NH2:28])=[CH:23][CH:22]=2)[N:10]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 66813324HCID 66813324, compound

Product 1

HCID 66813325HCID 66813325, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-aminoethyl)-3-{1-(4-sulfamoylphenyl)-5-p-tolyl-1H-pyrazol-3-yl}propanamide hydrochloride was reacted with N,N-diisopropylethylamine (DIPEA) in dichloromethane for 5 minutes at room temperature to produce N-(2-aminoethyl)-3-{1-(4-sulfamoylphenyl)-5-p-tolyl-1H-pyrazol-3-yl}propanamide which was then reacted with 5-(N-(14-carboxy-3,6,9,12-tetraoxatetradecyl)sulfamoyl)-2-(6-(diethylamino)-3-(diethyliminio)-3H-xanthen-9-yl)benzenesulfonate (produced as disclosed hereinabove with respect to Compound 27iii) in the presence of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCl), 1-hydroxybenzotriazole (HOBt), and N,N-diisopropylethylamine (DIPEA) in dichloromethane at room temperature to produce Compound 30f as a dark red solid (57% yield).

Sources & evidence

ORD record
ord-8b4a1ff304104e97912ca217c0261804
Source dataset
uspto-grants-2012_03
Patent number
US08143302B2

Reaction notes

Loading…