1-Bromo-2-Chloroethane → HCID 66689514, compound

HRID 337059Notes

Reaction equation

HRID 337059 reaction equation
[CH:1]1([NH:4][C:5](=[O:31])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]4([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=5[OH:29])[CH2:22][CH2:21]4)[C:14]3=[O:30])[CH:7]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][CH2:40][Cl:41]>C(#N)C>[Cl:41][CH2:40][CH2:39][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:20]1([NH:19][C:15]2[C:14](=[O:30])[N:13]([C:8]3[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=3[CH3:12])[C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)=[O:31])[CH:18]=[CH:17][N:16]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 66688774N-Cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide

Product 1

HCID 66689514HCID 66689514, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

To N-Cyclopropyl-3-(3-(1-(2-hydroxyphenyl)cyclopropylamino)-2-oxopyrazin-1(2H)-yl)-4-methylbenzamide (Example 167d, 0.34 g) in acetonitrile (5 mL) under nitrogen was added potassium carbonate (1.13 g) followed by 1-bromo-2-chloroethane (1.35 mL) and the reaction heated at 95° C. for 15 h. After cooling to rt the mixture was filtered through celite, and the solid cake washed with further acetonitrile. The filtrates were collected and the solvents removed in vacuo to give the subtitle product as a brown-orange solid (0.373 g).

Workup

  1. temperatureAfter cooling to rt the mixture
  2. filtrationwas filtered through celite
  3. washthe solid cake washed with further acetonitrile
  4. customThe filtrates were collected
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-f83c5d2d06d34372a8533e88b8ae9a3f
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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