1,2-Dichloroethane → HCID 86686956, compound

HRID 1402093Notes

Reaction equation

HRID 1402093 reaction equation
C(Cl)CCl.[C:5]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([OH:21])=O)[CH2:14][CH2:13]1)([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[F:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][NH2:30])=[N:27][CH:28]=1.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:8]([O:7][C:5]([N:12]1[CH2:13][CH2:14][N:15]([CH2:18][C:19]([NH:30][NH:29][C:26]2[CH:25]=[CH:24][C:23]([F:22])=[CH:28][N:27]=2)=[O:21])[CH2:16][CH2:17]1)=[O:6])([CH3:9])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 27356422-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}acetic acidHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 86686956HCID 86686956, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

EDC (543 mg, 2.83 mmol) was added portionwise to a solution of 2-(4-Boc-1-piperazinyl)acetic acid (576 mg, 2.36 mmol), 5-fluoro-2-hydrazinyl-pyridine (for reference procedure see WO 2010/022076, which is incorporated herein by reference in its entirety; 0.30 g, 2.36 mmol) and HOBt (32 mg, 0.24 mmol) in dry DCM (15 mL) at RT and stirred for 16 h. The solution was diluted with DCM (20 mL), washed with water (2×20 mL) and dried (Na2SO4). The solvent was evaporated to give the title compound as an off-white solid (667 mg, 80%). LCMS (Method 1): Rt 1.99 min, m/z 354 [MH+].

Workup

  1. washwashed with water (2×20 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-739897cdc47b4e48b705727caf8291bc
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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