Dichloromethane → HCID 58010059, compound

HRID 1854356Notes

Reaction equation

HRID 1854356 reaction equation
[NH:1]([C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]2=[N:7][CH:8]=1)[NH2:2].[N:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(Cl)Cl>C(Cl)(Cl)Cl>[S:12]([N:9]1[C:6]2=[N:7][CH:8]=[C:3]([NH:1][NH:2][C:28]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:29])[N:4]=[C:5]2[CH:11]=[CH:10]1)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:13])=[O:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2420851-Piperidinecarbonyl chlorideHCID 580098102-Hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 58010059HCID 58010059, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 25 mL round-bottomed flask was charged with 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.075 g, 0.25 mmol, Preparation #9) and TEA (0.041 mL, 0.29 mmol) in CHCl3 (1.2 mL) to give a brown suspension. Piperidine-1-carbonyl chloride (0.040 g, 0.27 mmol) was added and the reaction was stirred at ambient temperature for about 3 h. The reaction mixture was heated to about 45° C. for about 16 h. The mixture was cooled to ambient temperature, DCM (25 mL) was added, and the solution was washed with water and brine (about 5 mL each). The layers were separated and the organic solution was dried over anhydrous MgSO4, filtered, and concentrated to dryness under reduced pressure to give N′-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)piperidine-1-carbohydrazide (0.11 g, 100%): LC/MS (Table 2, Method a) Rt=2.09 min; MS m/z: 415 (M+H)+.

Workup

  1. customto give a brown suspension
  2. temperatureThe reaction mixture was heated to about 45° C. for about 16 h
  3. temperatureThe mixture was cooled to ambient temperature
  4. washthe solution was washed with water and brine (about 5 mL each)
  5. customThe layers were separated
  6. dry with materialthe organic solution was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6d6448bb13374cc39d75b127603eb12a
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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