Benzoyl chloride → HCID 11531921, compound

HRID 1443791Notes

Reaction equation

HRID 1443791 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][N:5]([C:10]1[N:15]=[N:14][C:13]([C:16]#[C:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=3)=[CH:12][CH:11]=1)[CH2:6]2.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH-].[Na+]>ClCCl>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][N:5]([C:10]1[N:15]=[N:14][C:13]([C:16]#[C:17][C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:22][CH:23]=3)=[CH:12][CH:11]=1)[CH2:6]2

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 11709521HCID 11709521, compound

Product 1

HCID 11531921HCID 11531921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 4-[6-(8-methyl-3,8-diaza-bicyclo[3.2.1]oct-3-yl)-pyridazin-3-ylethynyl]-phenylamine (0.53 g, 1.66 mmol) and dichloromethane (20 ml) was added: benzoylchloride (0.35 g, 2.5 mmol) solved in dichloromethane (20 ml). The mixture was stirred at 0° C. for 2 hours and was then allowed to stir at room temperature for 15 hours. Aqueous sodium hydroxide (20 ml, 1 M) was added and the mixture was extracted with dichloromethane (3×30 ml). The mixture was dried and evaporated. Mp 88-96° C. LC-ESI-HRMS of [M+H]+ shows 424.2145 Da. Calc. 424.213735 Da, dev. 1.8 ppm.

Workup

  1. additionwas added
  2. stirringto stir at room temperature for 15 hours
  3. extractionthe mixture was extracted with dichloromethane (3×30 ml)
  4. customThe mixture was dried
  5. customevaporated

Sources & evidence

ORD record
ord-ab9bacf617814f598dccc0d8ada21248
Source dataset
uspto-grants-2010_02
Patent number
US07662812B2

Reaction notes

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