1-Bromo-2-Chloroethane → 4-Chloro-3-[3-({1-[2-(2-chloroethoxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-N-cyclopropylbenzamide

HRID 337174Notes

Reaction equation

HRID 337174 reaction equation
[CH:1]([NH:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([N:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[OH:30])([CH3:23])[CH3:22])[C:15]2=[O:31])[CH:8]=1)(CC)[CH3:2].[C:33](=O)([O-])[O-].[K+].[K+].Br[CH2:40][CH2:41][Cl:42]>C(#N)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][CH:1]2[CH2:2][CH2:33]2)=[O:32])=[CH:8][C:9]=1[N:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[O:30][CH2:40][CH2:41][Cl:42])([CH3:22])[CH3:23])[C:15]1=[O:31]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 66689180N-(sec-butyl)-4-chloro-3-[3-{(1-(2-hydroxyphenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide

Product 1

HCID 666900194-Chloro-3-[3-({1-[2-(2-chloroethoxy)phenyl]-1-methylethyl}amino)-2-oxopyrazin-1(2H)-yl]-N-cyclopropylbenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A solution of N-(sec-butyl)-4-chloro-3-[3-{[1-(2-hydroxyphenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]benzamide (Example 330h, 1 g) dissolved in acetonitrile (10 mL) was treated with potassium carbonate (3.15 g) and 1-bromo-2-chloroethane (1.896 mL) under nitrogen. The resulting suspension was stirred at 75° C. for 10 h. The reaction mixture was evaporated to dryness, diluted with water (300 mL), and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and evaporated to afford the crude product. The crude product was triturated with 50% ether in isohexane to afford the subtitle compound (1.100 g).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additiondiluted with water (300 mL)
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product
  9. customThe crude product was triturated with 50% ether in isohexane

Sources & evidence

ORD record
ord-1fcc634c7d4d40db9e702e8e34f1f70b
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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