1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59725830, compound

HRID 545298Notes

Reaction equation

[N:1]1([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:19]1[CH2:23][CH2:22][C@@H:21]([OH:24])[CH2:20]1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[N:1]1([C:10]2[CH:11]=[CH:12][C:13]([C:14]([N:19]3[CH2:23][CH2:22][C@@H:21]([OH:24])[CH2:20]3)=[O:16])=[CH:17][CH:18]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-(1H-benzimidazol-1-yl)benzoic acid (2.88 g, 12.09 mmol) in DMF is treated with (3R)-pyrrolidin-3-ol (1.106 g, 12.69 mmol), 1-ethyl-3(3-dimethylaminopropyl)carbodiimide (2.78 g, 14.51 mmol) and N-hydroxybenzotriazole (1.89, 13.29 mmol), stirred at 80° C. for 12 hours and concentrated in vacuo. The resultant residue is dissolved in dichloromethane, washed sequentially with water and saturated NaCl, dried over MgSO4 and concentrated in vacuo to give a crude oil. Purification of this oil by flash column chromatography (silica, methanol:CH2Cl2 5:95) provides the title product as a white solid, 2.38 g (64% yield), identified by NMR and mass spectral analyses. (MS [308.4 m/e (M+H)].

Workup

concentrationconcentrated in vacuo
dissolutionThe resultant residue is dissolved in dichloromethane
washwashed sequentially with water and saturated NaCl
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give a crude oil
customPurification of this oil by flash column chromatography (silica, methanol:CH2Cl2 5:95)

Sources & evidence

ORD record: ord-26051528d69d4d8982f219cc32ad1ef0
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935719B2

Reaction notes

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