1,2-Dichloroethane → HCID 86686952, compound

HRID 2282363Notes

Reaction equation

HRID 2282363 reaction equation
C(Cl)CCl.[F:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][NH2:13])=[N:10][CH:11]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([C:27](O)=[O:28])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([C:27]([NH:13][NH:12][C:9]2[CH:8]=[CH:7][C:6]([F:5])=[CH:11][N:10]=2)=[O:28])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 199167865-Fluoro-2-hydrazinylpyridine

Product 1

HCID 86686952HCID 86686952, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDC (543 mg, 2.83 mmol) was added portionwise to a stirred solution of 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), piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (Aldrich, 649 mg, 2.83 mmol) and HOBt (32 mg, 0.24 mmol) in dry DCM (20 mL). The mixture was stirred at RT for 18 h. The solution was washed with water (2×20 mL), dried (Na2SO4) and evaporated. The residue was triturated (diethyl ether) to give the title compound as an off-white solid (713 mg, 82%). LCMS (Method 1): Rt 2.76 min, m/z 339 [MH+].

Workup

  1. washThe solution was washed with water (2×20 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was triturated (diethyl ether)

Sources & evidence

ORD record
ord-361168c4640c4fcb895c9587b996dd94
Source dataset
uspto-grants-2015_09
Patent number
US09139584B2

Reaction notes

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