Water → HCID 86687033, compound

HRID 1402172Notes

Reaction equation

HRID 1402172 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@@:3]1([CH3:10])[C:7]([OH:9])=O.[F:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][NH2:19])=[N:16][CH:17]=1.CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][NH:19][C:7]([C@:3]2([CH3:10])[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])=[O:9])=[N:16][CH:17]=1

Participants

8

Reactant 6

HCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 533022611,2-Dimethyl-L-proline

Product 1

HCID 86687033HCID 86687033, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (S)-1,2-dimethyl-pyrrolidine-2-carboxylic acid (660 mg, 4.61 mmol), (5-fluoro-pyridin-2-yl)-hydrazine (488 mg, 3.84 mmol) and Et3N (1.1 mL, 7.7 mmol) in DCM (20 mL) were added HOBt.H2O (51 mg, 0.38 mmol) and EDCI.HCl (884 mg, 4.61 mmol) and the mixture stirred at RT overnight. The mixture was partitioned between EtOAc/water and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. FCC, using 0-10% MeOH in DCM, gave the title compound as a brown solid (668 mg, 69%). LCMS (Method 4): Rt 0.40, m/z 253 [MH+].

Workup

  1. customThe mixture was partitioned between EtOAc/water
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7c639aee8db4c7682b9089abcea6c94
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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