1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11949716, compound

HRID 2356208Notes

Reaction equation

HRID 2356208 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[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19](O)=[O:20])[CH2:13][CH2:12]1)(=[O:10])=[O:9].CC[N:28]=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[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([NH2:28])=[O:20])[CH2:13][CH2:12]1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2723923Ammonium formateHCID 11949715HCID 11949715, compound

Product 1

HCID 11949716HCID 11949716, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-(2-Chlorophenylsulfonyl)piperazin-1-yl)benzoic acid (76 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, DMSO-D6) δ ppm 3.21 (s, 4 H), 3.31 (s, 4 H), 5.87 (br, s, 2 H), 6.68 (s, 1 H), 6.75 (s, 1 H), 6.90 (s, 1 H), 7.26 (s, 1 H), 7.59 (s, 1 H), 7.72 (s, 2 H), 8.02 (s, 1 H); ESI-MS: m/z 380.1 (M+H)+.

Sources & evidence

ORD record
ord-72d35c2faad342d9bedb4a42e69429cc
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

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