1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67479092, compound

HRID 2089248Notes

Reaction equation

HRID 2089248 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:5]2[C:4]([NH:15][CH2:16][C:17]([OH:19])=O)=[N:3]1.[NH2:20][CH:21]1[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=[C:5]2[C:4]([NH:15][CH2:16][C:17]([NH:20][CH:21]2[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24]2)=[O:19])=[N:3]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 67478798HCID 67478798, compound

Product 1

HCID 67479092HCID 67479092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask, was placed 2-((1-methyl-5-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)amino)acetic acid (as prepared in the previous step, 134 mg, 0.49 mmol) followed by DCM (20 mL), tert-butyl 3-aminoazetidine-1-carboxylate (104 mg, 0.60 mmol), EDCI (104 mg, 0.54 mmol) and HOBt (75 mg, 0.49 mmol). The reaction mixture was stirred overnight at room temperature and then concentrated in vacuo. The resulting residue was purified by flash chromatography (silica gel, 0-20% MeOH/ethyl acetate) to afford the title compound in sufficient purity to conduct the next step.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by flash chromatography (silica gel, 0-20% MeOH/ethyl acetate)

Sources & evidence

ORD record
ord-1f88402a48624131b0ae741e208fcb24
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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