Dimethyl Sulfoxide → HCID 59750672, compound

HRID 747975Notes

Reaction equation

HRID 747975 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:22][C:23]3[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[O:28])=[CH:25][N:24]=3)[CH:19]=2)[CH2:14]1.CCN(CC)CC>C(Cl)Cl>[CH:12]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:22][C:23]3[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[O:28])=[CH:25][N:24]=3)[CH:19]=2)[CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59750648HCID 59750648, compound

Product 1

HCID 59750672HCID 59750672, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Combine DCM (3 mL) and oxalyl chloride (41 uL) under nitrogen atmosphere at −78° C., and then add DMSO (49 uL) in DCM (2 mL). After the solution stirs for 15 minutes, add 6-(2-Hydroxymethyl-indan-5-yloxy)nicotinamide (33.1 mg, 0.116 mmol) in DCM (2 mL). After 15 minutes, add Et3N (97 uL, 0.70 mmol). After the reaction gradually warms to room temperature over the next 5 hours, then quench with water. Add the mixture to a separatory funnel and extract the product with DCM. Wash the organic phase with brine and then dry over Na2SO4. After concentrating under reduced pressure, flash chromatograph using 10% THF/CH2Cl2 eluent affords 27.4 mg, 0.10 mmol (84% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 3.1-3.2 (2H, m), 3.2-3.4 (3H, m), 6.8-7.0 (4H, m), 7.1-7.3 (1H, m), 8.8-8.9 (1H, m), 8.4 (1H, s), 9.7 (1H, s); TLC 1:6 THF:CH2Cl2 Rf:=0.7.

Workup

  1. customat −78° C.
  2. waitAfter 15 minutes
  3. customAfter the reaction
  4. customgradually warms to room temperature over the next 5 hours
  5. customquench with water
  6. additionAdd the mixture to a separatory funnel
  7. extractionextract the product with DCM
  8. washWash the organic phase with brine
  9. dry with materialdry over Na2SO4
  10. concentrationAfter concentrating under reduced pressure, flash chromatograph

Sources & evidence

ORD record
ord-2d71bc73960842e3a4c5932a9ab97257
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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