1,2-Dichloroethane → (4-Methyl-3-triisopropylsilanyloxymethyl-piperazin-1-yl)-acetic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

HRID 1402191Notes

Reaction equation

HRID 1402191 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([O-:11])=O)[CH2:4][CH:3]1[CH2:12][O:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16].[Na+].[F:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][NH2:33])=[N:30][CH:31]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl.O>[F:25][C:26]1[CH:27]=[CH:28][C:29]([NH:32][NH:33][C:9](=[O:11])[CH2:8][N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH:3]([CH2:12][O:13][Si:14]([CH:21]([CH3:22])[CH3:23])([CH:18]([CH3:19])[CH3:20])[CH:15]([CH3:16])[CH3:17])[CH2:4]2)=[N:30][CH:31]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 199167865-Fluoro-2-hydrazinylpyridineHCID 86687053Sodium (4-methyl-3-triisopropylsilanyloxymethyl-piperazin-1-yl)-acetate

Product 1

HCID 86687052(4-Methyl-3-triisopropylsilanyloxymethyl-piperazin-1-yl)-acetic acid N'-(5-fluoro-pyridin-2-yl)-hydrazide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of Intermediate 56b (390 mg, 1.06 mmol), (5-fluoro-pyridin-2-yl)-hydrazine (135 mg, 1.06 mmol) and HOBt.H2O (14.4 mg, 106 mop in DCM (15 mL) was added EDC (245 mg, 1.27 mmol) and stirred for 18 h. The mixture was washed with water, sat. aq. NaHCO3 and brine, and concentrated in vacuo to leave the title compound as a brown residue (412 mg, 86%). LCMS (Method 3): Rt 3.00 min, m/z 454 [MH+].

Workup

  1. washThe mixture was washed with water, sat. aq. NaHCO3 and brine
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ba49a2b6daf45258f3b1054ecdd0583
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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