1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58562579, compound

HRID 1896842Notes

Reaction equation

HRID 1896842 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=2)[N:19]=[CH:18][CH:17]=1)[CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.[NH2:41][CH:42]1[CH2:45][N:44]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:43]1.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]([C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=2)[N:19]=[CH:18][CH:17]=1)[CH2:12][C:13]([NH:41][CH:42]1[CH2:43][N:44]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:45]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 58562882HCID 58562882, compound

Product 1

HCID 58562579HCID 58562579, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(((benzyloxy)carbonyl)(6-(trifluoromethyl)quinolin-4-yl)amino)acetic acid (306 mg, 0.757 mmol, prepared in step F) and EDCI (217 mg, 1.13 mmol) in DCM (10 mL) was stirred until a clear solution resulted. This solution was added to a suspension of tert-butyl 3-aminoazetidine-1-carboxylate (156 mg, 0.908 mmol) and HOBt (116 mg, 0.757 mmol) in DCM (10 mL). The reaction mixture was stirred overnight at ambient temperature and poured onto saturated aqueous sodium bicarbonate, extracting with ethyl acetate. Concentration of the organic layer followed by purification of the residue by flash chromatography (silica gel, 0-20% MeOH/ethyl acetate) afforded the product.

Workup

  1. customresulted
  2. extractionextracting with ethyl acetate
  3. customConcentration of the organic layer followed by purification of the residue by flash chromatography (silica gel, 0-20% MeOH/ethyl acetate)
  4. customafforded the product

Sources & evidence

ORD record
ord-077d3a00603d4569871128af3c597cda
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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