Dimethylformamide → HCID 69735824, compound

HRID 1063173Notes

Reaction equation

HRID 1063173 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[Cl:22])[CH:14]=2)=[O:12])=[CH:5][CH:4]=1.[CH3:23]N(C=O)C>>[CH3:23][N:10]([CH2:9][C:6]1[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=1)[C:11]([C:13]1[S:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][C:19]=2[Cl:22])[CH:14]=1)=[O:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 85797600HCID 85797600, compound

Product 1

HCID 69735824HCID 69735824, compoundYield 23%

Procedure

NaH (0.244 g, 6.09 mmol) was added to a solution of 7-chloro-thieno[3,2-b]pyridin-2-carboxylic acid (pyridin-4-ylmethyl)-amide (0.616 g, 2.03 mmol, prepared as described in Example 11) in DMF (10 mL). When the effervescence ceased, Mel (0.576 g, 4.06 mmol) was added dropwise. After 3 h the reaction mixture was quenched with saturated aqueous KCN (10 mL). The aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4), and the solvent was removed under reduced pressure. Purification by flash chromatography on silica gel (CH2Cl2/MeOH 94:6) afforded the title compound as a yellow oil (0.15 g, 23%). MS: 318.0/320.0 (MH+); HPLC Rf: 4.24 min; HPLC purity: 93%.

Workup

  1. additionMel (0.576 g, 4.06 mmol) was added dropwise
  2. customAfter 3 h the reaction mixture was quenched with saturated aqueous KCN (10 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. customthe solvent was removed under reduced pressure
  6. customPurification by flash chromatography on silica gel (CH2Cl2/MeOH 94:6)

Sources & evidence

ORD record
ord-b12ec2f41928432093bb57233b0ea06e
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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