Water → HCID 86687033, compound

HRID 630759Notes

Reaction equation

HRID 630759 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-d26fde8da6eb4ba2ace47fb76defb685
Source dataset
uspto-grants-2016_04
Patent number
US09315503B2

Reaction notes

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