1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69374413, compound

HRID 1249774Notes

Reaction equation

[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](O)=[O:13])=[CH:2]1.C([N:24](CC)C(C)C)(C)C.[NH4+].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>ClCCl>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([NH2:24])=[O:13])=[CH:2]1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 264 mg (1 mmol.) of 3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2-phenyl-2-propenoic acid in 1.5 ml of THFd and 3 ml of DMFd was added 350 μl of N,N-diisopropylethylamine and 154 mg (1.4 mmol.) of N-hydroxybenzotriazole ammonium salt. The obtained mixture was cooled to −20° C. and 266 mg (1.4 mmol.) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide were added. The reaction mixture was stirred for 2 hours at −20° C. and then warmed to room temperature. After additional 12 hours, the organic layer was diluted with dichloromethane, washed with saturated sodium bicarbonate, brine, dried over sodium sulphate and evaporated. The residual solid was triturated with EtOAc to afford 76 mg of the title compound as a white solid (yield 29%) m.p. 222-224° C.

Workup

temperaturewarmed to room temperature
waitAfter additional 12 hours
washwashed with saturated sodium bicarbonate, brine
dry with materialdried over sodium sulphate
customevaporated
customThe residual solid was triturated with EtOAc

Sources & evidence

ORD record: ord-8d00b7a2446147d38ebc3de51488ab7a
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06335342B1

Reaction notes

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