2-Bromoacetamide → HCID 86612503, compound

HRID 2053099Notes

Reaction equation

HRID 2053099 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:19]=[C:18]([C:28]#[N:29])[N:17]=2)=[CH:12][C:11]=1[C:30]([F:33])([F:32])[F:31].C(N(C(C)C)CC)(C)C.Br[CH2:44][C:45]([NH2:47])=[O:46]>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:28]([C:18]1[N:19]=[C:20]([N:22]2[CH2:23][CH2:24][N:25]([CH2:44][C:45]([NH2:47])=[O:46])[CH2:26][CH2:27]2)[CH:21]=[C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[C:11]([C:30]([F:31])([F:33])[F:32])[CH:12]=2)[N:17]=1)#[N:29]

Participants

5

Reactant 3

HCID 696322-BromoacetamideHCID 81531DiisopropylethylamineHCID 86612504HCID 86612504, compound

Product 1

HCID 86612503HCID 86612503, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

4-(4-Methoxy-3-trifluoromethyl-phenyl)-6-piperazin-1-yl-pyrimidine-2-carbonitrile trifluoroacetic acid salt (50 mg), diisopropylethylamine (40 mg) and 2-bromoacetamide (22 mg) were dissolved in acetonitrile (2 ml) and the mixture was stirred at 65° C. overnight. Mixture was partitioned between ethyl acetate (10 ml) and water (10 ml), organics were dried and evaporated under reduced pressure to afford a white solid. Purification by prep-HPLC afforded 18 mg of 2-{4-[2-Cyano-6-(4-methoxy-3-trifluoromethyl-phenyl)-pyrimidin-4-yl]-piperazin-1-yl}-acetamide trifluoroacetic acid salt as a white solid.

Workup

  1. customMixture was partitioned between ethyl acetate (10 ml) and water (10 ml)
  2. customorganics were dried
  3. customevaporated under reduced pressure
  4. customto afford a white solid
  5. customPurification

Sources & evidence

ORD record
ord-5dcaf168f66f438d86c8dffa8d517f8b
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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