1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44814425, compound

HRID 450112Notes

Reaction equation

HRID 450112 reaction equation
Cl.[C:2]12([C:8]3[C:16]4[C:11](=[N:12][CH:13]=[CH:14][CH:15]=4)[NH:10][CH:9]=3)[CH2:7][CH:6]1[CH2:5][NH:4][CH2:3]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[F:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2([C:48](O)=[O:49])[CH2:47][CH2:46]2)=[CH:41][CH:40]=1>C(Cl)Cl.CN(C=O)C.C(N(CC)CC)C>[F:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2([C:48]([N:4]3[CH2:5][CH:6]4[C:2]([C:8]5[C:16]6[C:11](=[N:12][CH:13]=[CH:14][CH:15]=6)[NH:10][CH:9]=5)([CH2:7]4)[CH2:3]3)=[O:49])[CH2:46][CH2:47]2)=[CH:43][CH:44]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 64842201-(4-fluorophenyl)cyclopropanecarboxylic acidHCID 67172481HCID 67172481, compound

Product 1

HCID 44814425HCID 44814425, compoundYield 40.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

3-(3-azabicyclo[3.1.0]hex-1-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride (60 mg, 0.3 mmol) was dissolved in DCM (3 ml) and a few drops of DMF, and cooled to 0° C. Then HOBt (38 mg, 0.33 mmol), EDCI (54 mg, 0.33 mmol) were added followed by triethylamine (106 μL) and 1-(4-fluorophenyl)cyclopropanecarboxylic acid (46 mg, 0.3 mmol). The mixture was stirred at RT overnight. The volatiles were removed in vacuo and the residue was purified by column chromatography (DCM/MeOH 97:3) to yield the title compound as a yellow solid (44 mg).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by column chromatography (DCM/MeOH 97:3)

Sources & evidence

ORD record
ord-48a1d0b2572b409eb6b78e9941781681
Source dataset
uspto-grants-2013_07
Patent number
US08486964B2

Reaction notes

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