1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67278220, compound

HRID 1696228Notes

Reaction equation

[CH:1]1([NH:7][C:8]2[C:13]([C:14]([OH:16])=O)=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[N:21]1[C:25]2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.CN>CN(C)C=O.CCOC(C)=O.O>[CH:1]1([NH:7][C:8]2[C:13]([C:14]([NH:21][CH3:25])=[O:16])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 4-(cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (25 mg) in N,N-dimethylformamide (0.375 mL) were added 1-hydroxybenzotriazole (19.5 mg),1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (22.5 mg) and methylamine hydrochloride (9.8 mg). The mixture was stirred at 55° C. for 1 hour. To the solution were added water and EtOAc and the mixture was extracted with EtOAc. The extract was washed with water, dried over MgSO4, filtrated and evaporated The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-(cyclohexylamino)-N-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (5 mg), as a pale yellow powder.

Workup

extractionthe mixture was extracted with EtOAc
washThe extract was washed with water
dry with materialdried over MgSO4
filtrationfiltrated
customevaporated The residue
customwas purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10)

Sources & evidence

ORD record: ord-9cf1f04b9a6a4516a3396bfc2e75a952
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163767B2

Reaction notes

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