1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 117729238, compound

HRID 2200061Notes

Reaction equation

HRID 2200061 reaction equation
[CH3:1][N:2]([CH3:12])[C@@H:3]1[CH2:7][N:6]([CH3:8])[C@H:5]([C:9]([OH:11])=O)[CH2:4]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[F:34][C:35]1[CH:36]=[CH:37][C:38]([NH:41][NH2:42])=[N:39][CH:40]=1>C(Cl)Cl>[F:34][C:35]1[CH:36]=[CH:37][C:38]([NH:41][NH:42][C:9]([C@@H:5]2[CH2:4][C@H:3]([N:2]([CH3:1])[CH3:12])[CH2:7][N:6]2[CH3:8])=[O:11])=[N:39][CH:40]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 117728947HCID 117728947, compound

Product 1

HCID 117729238HCID 117729238, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Intermediate 38a (5.95 g, 34.2 mmol) in DCM (60 mL) was treated with EDCI (7.87 g, 34.2 mmol), HOBt (0.462 g, 41.0 mmol) and (5-fluoro-pyridin-2-yl)-hydrazine (4.35g g, 34.2 mmol) and the solution was stirred at RT for 16 hours. The reaction mixture was partitioned between H2O (50 mL) and DCM (40 mL) and the phases were separated. The organic phase was washed with sat. bicarbonate solution and the brine. The volatiles were concentrated in vacuo and the resultant residue was purified by FCC using 0-10% MeOH in DCM to afford the title compound (1.74 g, 20%). LCMS (Method 3): Rt 0.44 min, m/z 282 [MH+].

Workup

  1. customThe reaction mixture was partitioned between H2O (50 mL) and DCM (40 mL)
  2. customthe phases were separated
  3. washThe organic phase was washed with sat. bicarbonate solution
  4. concentrationThe volatiles were concentrated in vacuo
  5. customthe resultant residue was purified by FCC

Sources & evidence

ORD record
ord-cdf9e33dee5f4b69ba665f32d6c0f3d5
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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