Dimethyl Sulfoxide → HCID 178430848, compound

HRID 714342Notes

Reaction equation

HRID 714342 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][CH:12]1[CH2:16][NH:15][C:14]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:18]=2)=[N:13]1.C(N(CC)CC)C>ClCCl>[CH3:11][C:12]1[N:13]=[C:14]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24](=[O:31])[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:18]=2)[NH:15][CH:16]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178430407HCID 178430407, compound

Product 1

HCID 178430848HCID 178430848, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (0.06 mL, 0.72 mmol) in anhydrous dichloromethane (1.0 mL) was added anhydrous dimethyl sulfoxide (0.09 mL, 1.20 mmol) dropwise at −78° C. under nitrogen atmosphere. The resulting solution was stirred for 10 minutes, followed by dropwise addition of a solution of N-(4-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)pyridin-2-yl)benzamide (0.17 g, 0.60 mmol) in anhydrous dichloromethane (1.5 mL). The reaction mixture was stirred for 40 minutes, followed by the addition of anhydrous triethyl amine (0.33 mL, 2.38 mmol), warmed to ambient temperature during 3 hours and partitioned between water (15 mL) and dichloromethane (25 mL). The aqueous layer was extracted with dichloromethane (2×25 mL). The organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography eluting with ethyl acetate followed by methanol in ethyl acetate (1:25 ratio) to give N-(4-(4-methyl-1H-imidazol-2-yl)pyridin-2-yl)benzamide as a colorless solid (0.05 g, 38%): mp 133-135° C.; 1H NMR (300 MHz, DMSO-d6) δ 12.70 (s, 1H), 10.81 (s, 1H), 8.69 (s, 1H), 8.40 (d, J=5.3 Hz, 1H), 8.08-8.03 (m, 2H), 7.64-7.49 (m, 4H), 6.95 (br s, 1H), 2.24 (s, 3H); 13C NMR (75 MHz, CD3OD) δ 168.5, 154.1, 149.8, 144.5, 140.8, 135.6, 133.4, 129.8, 128.8, 116.9, 111.4, 11.6; MS (ES+) m/z 279.4 (M+1).

Workup

  1. stirringThe reaction mixture was stirred for 40 minutes
  2. custompartitioned between water (15 mL) and dichloromethane (25 mL)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×25 mL)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to dryness
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-aa09633d6bd845f39a50ffb02c1873e3
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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