1,2-Dichloroethane → 3-Pyrrolidin-1-yl-propionic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 2282353Notes

Reaction equation

HRID 2282353 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.Cl.[N:11]1([CH2:16][CH2:17][C:18](O)=[O:19])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH:9][C:18](=[O:19])[CH2:17][CH2:16][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 177503823-(Pyrrolidin-1-yl)propanoic acid--hydrogen chloride (1/1)HCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 866869443-Pyrrolidin-1-yl-propionic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-fluoro-2-hydrazinopyridine (285 mg, 2.24 mmol) and 3-(pyrrolidin-1-yl)propanoic acid hydrochloride (400 mg, 2.24 mmol) were dissolved in DMF (15 mL). EDC (516 mg, 2.69 mmol), HOBt (30.0 mg, 0.22 mmol) and triethylamine (374 μL, 2.69 mmol) were added and the reaction stirred for 18 h. The mixture was loaded onto an SCX-2 cartridge, which was washed with MeOH then with 2M NH3 in MeOH. The basic fractions were evaporated in vacuo then purified by FCC using 0-10% [2M NH3 in MeOH] in DCM to give the title compound contaminated with several impurities (400 mg). The product was used in the next step without further purification.

Workup

  1. washwas washed with MeOH
  2. customThe basic fractions were evaporated in vacuo
  3. customthen purified by FCC

Sources & evidence

ORD record
ord-6fb3992707a3497cbf5ec61cc8ac4c05
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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