Hydroxyamine hydrochloride → HCID 136332522, compound

HRID 2233992Notes

Reaction equation

HRID 2233992 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[C:22]([C:24]#[N:25])[N:21]=[C:20]([Cl:26])[N:19]=2)[CH2:14][CH2:13]1)=[O:10].Cl.[NH2:28][OH:29]>CO.CCOC(C)=O>[NH2:25]/[C:24](=[N:28]\[OH:29])/[C:22]1[N:21]=[C:20]([Cl:26])[N:19]=[C:18]([N:15]2[CH2:16][CH2:17][CH:12]([NH:11][C:9]([C:3]3[NH:4][C:5]([CH3:8])=[C:6]([Cl:7])[C:2]=3[Cl:1])=[O:10])[CH2:13][CH2:14]2)[CH:23]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86608334HCID 86608334, compound

Product 1

HCID 136332522HCID 136332522, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3,4-Dichloro-N-[1-(2-chloro-6-cyanopyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (Example 199, 150 mg, 0.36 mmol), hydroxylamine hydrochloride (25 mg, 0.36 mmol) and TEA (0.05 ml, 0.36 mmol) were combined in MeOH (5 ml), and the reaction was heated at 80° C. for 2 h. The reaction was diluted with EtOAc and washed with water. The aqueous portion was extracted with EtOAc, and the combined organic portions were dried (sodium sulfate), filtered and concentrated to give a pale yellow solid. The crude material was purified by preparatory HPLC, using a gradient of 35-75% acetonitrile/water (0.1% TFA) to give 53 mg of the title compound.

Workup

  1. washwashed with water
  2. extractionThe aqueous portion was extracted with EtOAc
  3. dry with materialthe combined organic portions were dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a pale yellow solid
  7. customThe crude material was purified by preparatory HPLC

Sources & evidence

ORD record
ord-764f26fe5c1346f0ac514a4af83f9b25
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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