Bromoacetonitrile → HCID 10159427, compound

HRID 1178554Notes

Reaction equation

HRID 1178554 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[C:11]1[N:12]=[C:13]([C:17]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[OH:26])[CH2:19][CH2:18]2)[S:14][C:15]=1[CH3:16].[H-].[Na+].Br[CH2:30][C:31]#[N:32]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[C:11]1[N:12]=[C:13]([C:17]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH2:30][C:31]#[N:32])[CH2:19][CH2:18]2)[S:14][C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 69517162HCID 69517162, compound

Product 1

HCID 10159427HCID 10159427, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{1-[4-(2-Chloro-4-methoxy-5-methyl-phenyl)-5-methyl-thiazol-2-yl]-cyclopropyl}-phenol (Example 126) (15 mg, 0.04 mmol) was dissolved in tetrahydrofuran (THF) (1 ml), treated with 1.1 mg NaH (0.044 mmol) at room temperature and stirred for 30 min. Bromoacetonitrile (5.5 mg, 0.044 mmol) was then added to the reaction vessel. The reaction mixtures was stirred overnight. The reaction mixture was quenched with 0.5 ml water and the THF removed in vacuo The residue was partitioned between ethyl acetate and water and the organic solution was separated and concentrated in vacuo then dissolved in methanol/dimethylsulfoxide (DMSO) 1:1 and purified via reversed phase HPLC chromatography (vide supra). Yield 11.5 mg (68%). [MH]+ 425.0, 427.0.

Workup

  1. customThe reaction mixtures
  2. stirringwas stirred overnight
  3. customThe reaction mixture was quenched with 0.5 ml water
  4. customthe THF removed in vacuo The residue
  5. customwas partitioned between ethyl acetate and water
  6. customthe organic solution was separated
  7. concentrationconcentrated in vacuo
  8. dissolutionthen dissolved in methanol/dimethylsulfoxide (DMSO) 1:1
  9. custompurified

Sources & evidence

ORD record
ord-19c2bec4a019414b95bfadb8d9864394
Source dataset
uspto-grants-2007_10
Patent number
US07276526B2

Reaction notes

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