Chloroacetyl chloride → HCID 22346327, compound

HRID 897314Notes

Reaction equation

HRID 897314 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:13]1[N:22]=[C:21]([C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[O:24])[C:20]([OH:34])=[C:19]2[C:14]=1[CH:15]=[CH:16][CH:17]=[N:18]2)(C)(C)C.C(NCC)(C)C.[Cl:42][CH2:43][C:44](Cl)=[O:45]>O1CCOCC1>[F:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][NH:25][C:23]([C:21]2[C:20]([OH:34])=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[N:18]3)=[C:13]([CH2:12][CH2:11][N:10]([CH2:9][CH2:8][NH2:7])[C:44](=[O:45])[CH2:43][Cl:42])[N:22]=2)=[O:24])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 88318IsopropylethylamineHCID 20816895HCID 20816895, compound

Product 1

HCID 22346327HCID 22346327, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-Butyl-2-{[2-(7-{[(4-fluorobenzyl)amino]carbonyl}-8-hydroxy[1,6]-naphthyridin-5-yl)ethyl]amino}ethylcarbamate (Example 150, Step 1) (0.10 g, 0.21 mmol), isopropylethylamine (0.11 mL, 0.62 mmol), and chloroacetyl chloride (18 μL, 0.23 mmol) in dioxane (10 mL) was stirred at room temperature for 1 hour. The resultant mixture was concentrated under vacuum. The residue was dissolved in dichloromethane (5 mL) and treated with trifluoroacetic acid (0.5 mL) and stirred at room temperature overnight. The resultant mixture was concentrated under vacuum and used in the following step without further purification. ES MS M+1=406

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum
  2. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  3. additiontreated with trifluoroacetic acid (0.5 mL)
  4. stirringstirred at room temperature overnight
  5. concentrationThe resultant mixture was concentrated under vacuum
  6. customused in the following step without further purification

Sources & evidence

ORD record
ord-0a26e1c700e641bca330dcbc5cbb3d2f
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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