Benzoyl chloride → HCID 17817694, compound

HRID 1824715Notes

Reaction equation

HRID 1824715 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:19]S(C)(=O)=O)[C:6]2[O:10][C:9]([N:11]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:8][C:7]=2[CH:18]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C>[ClH:2].[C:31]([NH:19][C:5]1[C:6]2[O:10][C:9]([N:11]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:8][C:7]=2[CH:18]=[C:3]([Cl:2])[CH:4]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 69635522HCID 69635522, compound

Product 1

HCID 17817694HCID 17817694, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 14 (a) (7-amino-5-chloro-2-[1-(4-tert-butyloxycarbonyl) homopiperazinyl]benzoxazole, 48 mg, 0.130 mmol) was dissolved in methylene chloride (2 ml), and the solution was successively added with triethylamine (0.056 ml) and benzoyl chloride (0.031 ml) at 0° C. After the reaction mixture was stirred for 3 hours, the reaction was stopped by using saturated aqueous solution of sodium hydrogencarbonate. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solution was added with 4 N hydrochloric acid in ethyl acetate (1 ml), and the deposited solids were collected by filtration to obtain the title compound (20 mg).

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. additionThe solution was added with 4 N hydrochloric acid in ethyl acetate (1 ml)
  4. filtrationthe deposited solids were collected by filtration

Sources & evidence

ORD record
ord-d5fb76874177481ba87f0dbb2007330c
Source dataset
uspto-grants-2006_05
Patent number
US07045516B1

Reaction notes

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