1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 46241323, compound

HRID 2096163Notes

Reaction equation

HRID 2096163 reaction equation
O[C:2]([C:4]([F:7])([F:6])[F:5])=O.[NH2:8][CH:9]1[CH2:12][N:11]([CH:13]2[CH2:18][CH2:17][C:16]([C:20]3[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)([OH:19])[CH2:15][CH2:14]2)[CH2:10]1.C(O[C:33]([NH:35][CH2:36][C:37]([OH:39])=O)=[O:34])(C)(C)C.CCN=C=NCCCN(C)C.[CH:51]1[CH:52]=[CH:53]C2N(O)N=N[C:55]=2[CH:56]=1>C(Cl)Cl>[OH:19][C:16]1([C:20]2[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH2:15][CH2:14][CH:13]([N:11]2[CH2:10][CH:9]([NH:8][C:37]([CH2:36][NH:35][C:33](=[O:34])[C:51]3[CH:52]=[CH:53][C:2]([C:4]([F:7])([F:6])[F:5])=[CH:55][CH:56]=3)=[O:39])[CH2:12]2)[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 86642252HCID 86642252, compound

Product 1

HCID 46241323HCID 46241323, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Amino-azetidin-1-yl)-1-(6-methoxy-pyridin-3-yl)-cyclohexanol TFA salt (˜4.2 g, 15.1 mmol), tert-butoxycarbonylamino-acetic acid (Sigma, 2.70 g, 15.1 mmol) and TEA (4.20 mL, 30 mmol) were dissolved in DCM (30 mL) at room temperature. The mixture was then treated with EDCI (Aldrich, 3.05 g, 16 mmol) and HOBT (Aldrich, 2.16 g, 16 mmol). And the reaction was stirred at room temperature for additional 6 hours. The reaction solution was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was then purified by CombiFlash® system DCM and MeOH MeOH as eluent (from pure DCM to 10% MeOH in DCM) to afford the title compound as a white solid.

Workup

  1. customThe reaction solution was partitioned between DCM and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas then purified by CombiFlash® system DCM and MeOH MeOH as eluent (from pure DCM to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-5d413b09c41c4101bfbc056112a5e6e1
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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