Dichloromethane → HCID 59850202, compound

HRID 2064174Notes

Reaction equation

HRID 2064174 reaction equation
[Br:1][C:2]1[C:3]([C:18]([F:21])([F:20])[F:19])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:6]=2[CH:17]=1.[CH3:22][C:23]([CH3:27])(O)[C:24]#[N:25].S([O-])([O-])(=O)=O.[Mg+2].Cl[CH2:35]Cl.CN(C)[C:39](=[O:41])C>>[Br:1][C:2]1[C:3]([C:18]([F:21])([F:20])[F:19])=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([CH:11]3[CH2:12][CH2:13][N:14]([C:23]4([C:24]#[N:25])[CH2:27][CH2:39][O:41][CH2:35][CH2:22]4)[CH2:15][CH2:16]3)[C:6]=2[CH:17]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 6406Acetone CyanohydrinHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31374DimethylacetamideHCID 59850200HCID 59850200, compound

Product 1

HCID 59850202HCID 59850202, compound

Conditions

Temperature
60 °C

Procedure

A stirred solution of 6-bromo-1-(4-piperidinyl)-5-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one (free base of D69, 0.28 g, 0.77 mmol) in N,N-dimethylacetamide (3 ml) at room temperature under argon was treated with acetone cyanohydrin (0.13 g, 1.5 mmol) and dry magnesium sulphate (0.50 g), then heated at 60° C. whilst a gentle stream of argon was passed over the well stirred mixture. After 48 hrs the mixture containing a thick pale yellow precipitate was cooled to room temperature and treated with dichloromethane (25 ml), then stirred for 15 minutes. The liquid which contained the fine suspension of the solid precipitate was decanted off from the magnesium sulphate which had settled to the base of the flask. The decanted mixture was then filtered to afford the title compound as a white solid (>90% purity) (0.24 g, 66%).

Workup

  1. additionAfter 48 hrs the mixture containing a thick pale yellow precipitate
  2. temperaturewas cooled to room temperature
  3. stirringstirred for 15 minutes
  4. additionthe fine suspension of the solid precipitate
  5. customwas decanted off from the magnesium sulphate which
  6. filtrationThe decanted mixture was then filtered

Sources & evidence

ORD record
ord-3ddc12bb9c1147fa8803f4bec37fe1e3
Source dataset
uspto-grants-2012_10
Patent number
US08288412B2

Reaction notes

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