1,2-Dichloroethane → HCID 68292092, compound

HRID 1507994Notes

Reaction equation

HRID 1507994 reaction equation
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13](O)=[O:14])[CH:12]=[C:6]2[C:5]=1[NH:16][C@@H:17]([C:19]1([CH3:22])[CH2:21][CH2:20]1)[CH3:18])(=[O:3])[NH2:2].C1C=CC2N(O)[N:30]=[N:29]C=2C=1.C(Cl)CCl.NN>CN(C=O)C.O>[NH:29]([C:13]([C:11]1[CH:12]=[C:6]2[C:5]([NH:16][C@@H:17]([C:19]3([CH3:22])[CH2:20][CH2:21]3)[CH3:18])=[C:4]([C:1]([NH2:2])=[O:3])[CH:9]=[N:8][N:7]2[CH:10]=1)=[O:14])[NH2:30]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 9321HydrazineHCID 757711-HydroxybenzotriazoleHCID 68291613HCID 68291613, compound

Product 1

HCID 68292092HCID 68292092, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (R)-3-carbamoyl-4-((1-(1-methylcyclopropyl)ethyl)amino)pyrrolo[1,2-b]pyridazine-6-carboxylic acid (1.11 g, 3.67 mmol) in DMF (Volume: 10 mL) was added HOBT (0.675 g, 4.41 mmol) and EDC (0.915 g, 4.77 mmol) which was stirred at 23° C. for 1 hr. To the reaction mixture was added hydrazine (0.576 mL, 18.36 mmol) dropwise and stirred for 30 minutes, followed by the addition of 50 mL of water and stirred for 20 minutes. The solid was collected as the desired product (1.54 g). MS (ES+) m/z: 317.08 (M+H); HPLC: 91%, retention time: 1.935 min (analytical HPLC Method B).

Workup

  1. stirringstirred for 30 minutes
  2. stirringstirred for 20 minutes
  3. customThe solid was collected as the desired product (1.54 g)

Sources & evidence

ORD record
ord-5f9ee2bd50ab43668654154cdd6263f7
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

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