1,2-Dichloroethane → 4-Morpholin-4-ylmethyl-benzoic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 1402113Notes

Reaction equation

HRID 1402113 reaction equation
C1C=CC2N(O)N=NC=2C=1.[F:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][NH2:19])=[N:16][CH:17]=1.[N:20]1([CH2:26][C:27]2[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(Cl)CCl>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][NH:19][C:31](=[O:32])[C:30]2[CH:29]=[CH:28][C:27]([CH2:26][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[CH:35][CH:34]=2)=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 7035074-(morpholinomethyl)benzoic acidHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 866869794-Morpholin-4-ylmethyl-benzoic acid N'-(5-fluoro-pyridin-2-yl)-hydrazideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HOBt (53 mg, 0.39 mmol) was added to (5-fluoro-pyridin-2-yl)-hydrazine (for reference procedure see WO 2010/022076, which is incorporated herein by reference in its entirety; 500 mg, 3.94 mmol), 4-morpholin-4-ylmethyl-benzoic acid (1.04 g, 4.72 mmol) and EDC (907 mg, 4.72 mmol) in DCM (5.0 mL) and the reaction stirred for 4 h. The reaction was partitioned between DCM (75 mL) and saturated aqueous NaHCO3 (75 mL) and the aqueous layer extracted with DCM (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo then purified by FCC using [0.5-7.5% 2M NH3 in MeOH] in DCM to give the title compound (980 mg, 2.97 mmol, 75%). LCMS (Method 4): Rt 0.27, m/z 331 [MH+].

Workup

  1. customThe reaction was partitioned between DCM (75 mL) and saturated aqueous NaHCO3 (75 mL)
  2. extractionthe aqueous layer extracted with DCM (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customthen purified by FCC

Sources & evidence

ORD record
ord-8ecd386a38ea402ea1a571576df974a8
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

Loading…