Dimethylformamide → 3,4-Dichloro-N-{1-[2-chloro-6-(hydrazinocarbonyl)pyrimidin-4-yl]piperidin-4-yl}-5-methyl-1H-pyrrole-2-carboxamide

HRID 2233986Notes

Reaction equation

HRID 2233986 reaction equation
[Cl:1][C:2]1[NH:7][C:6]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]3[NH:22][C:23]([CH3:28])=[C:24]([Cl:27])[C:25]=3[Cl:26])=[O:20])[CH2:14][CH2:13]2)(C(OC)=O)[CH:5]=[CH:4][N:3]=1.[NH2:29]N.C[N:32]([CH:34]=[O:35])C>>[Cl:26][C:25]1[C:24]([Cl:27])=[C:23]([CH3:28])[NH:22][C:21]=1[C:19]([NH:18][CH:15]1[CH2:16][CH2:17][N:12]([C:6]2[CH:5]=[C:4]([C:34]([NH:32][NH2:29])=[O:35])[N:3]=[C:2]([Cl:1])[N:7]=2)[CH2:13][CH2:14]1)=[O:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 9321HydrazineHCID 178499026HCID 178499026, compound

Product 1

HCID 866083313,4-Dichloro-N-{1-[2-chloro-6-(hydrazinocarbonyl)pyrimidin-4-yl]piperidin-4-yl}-5-methyl-1H-pyrrole-2-carboxamide

Procedure

Methyl 2-chloro-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrimidine-4-carboxylate (Example 6) (500 mg, 1.12 mmol), hydrazine (0.035 ml, 1.12 mmol), and TEA (0.16 ml, 1.12 mmol) were combined in DMF (3 ml) and stirred at room temperature. Within 1.5 h, a white precipitate had formed. The reaction was stirred for another 30 minutes, and then the precipitate was collected by suction filtration to give 377 mg of the title compound. 100 mg of the crude material was purified by preparatory HPLC, using a gradient of 40-70% acetonitrile/water (0.1% TFA) over 14 minutes to give 23 mg of the title compound.

Workup

  1. customa white precipitate had formed
  2. stirringThe reaction was stirred for another 30 minutes
  3. filtrationthe precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-ba12524ced0e48a2b3ba2c3800063345
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

Loading…