1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58724206, compound

HRID 2356209Notes

Reaction equation

HRID 2356209 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]([OH:24])=O)[N:21]=2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].CC[N:27]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])=O.[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]([NH2:27])=[O:24])[N:21]=2)[CH2:13][CH2:12]1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2723923Ammonium formateHCID 58724173HCID 58724173, compound

Product 1

HCID 58724206HCID 58724206, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-(2-chlorophenylsulfonyl)piperazin-1-yl)thiazole-4-carboxylic acid (77 mg, 0.02 mmole), EDCI (39 mg, 0.02 mmole), HOBt (31 mg, 0.02 mmole) and ammonium formate (13 mg, 0.02 mmole) were combined in 1 ml of dry DMF. The mixture was treated with 1 equivalent of TEA and stirred at room temperature overnight. The title compound was obtained in yield of 37% after purification on preparative HPLC. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 3.41 (s, 1 H), 3.42-3.44 (m, 3 H), 3.53-3.56 (m, 3 H), 3.57 (s, 1 H), 6.02 (s, 1 H), 6.95 (s, 1 H), 7.38-7.44 (m, 2 H), 7.50-7.53 (m, 2 H), 8.02-8.07 (m, 1 H); ESI-MS: m/z 387.1 (M+H)+.

Sources & evidence

ORD record
ord-24eb19526d334528b62e61f074f7b6c5
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

Loading…