Dimethyl Sulfoxide → HCID 66920719, compound

HRID 1364563Notes

Reaction equation

HRID 1364563 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:18]=[N:19][C:20](Cl)=[CH:21][CH:22]=2)=[O:14])[CH:3]=1.[CH3:24][S:25](C)=O>>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:18]=[N:19][C:20]([S:25][CH3:24])=[CH:21][CH:22]=2)=[O:14])[CH:3]=1

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 87205321HCID 87205321, compound

Product 1

HCID 66920719HCID 66920719, compound

Procedure

A solution of Example 185 (70 mg, 0.21 mmol) and sodium methylthiolate (32 mg, 0.46 mmol) in dimethyl sulfoxide (0.8 mL) was heated to 90° C. for 12 h., extracted with ethyl acetate (5 mL), and washed with H2O (2×5 mL). The organic layer was concentrated in vacuo and purified by silica gel chromatography (50-100% ethyl acetate in hexanes) providing the title compound as an off white solid (42 mg, 58%). 1H NMR (300 MHz, DMSO-d6) δ 8.98-9.15 (m, 1H), 8.32-8.44 (m, 1H), 7.57 (dd, J=8.31, 2.20 Hz, 1H), 7.32 (s, 2H), 7.25 (dd, J=8.31, 0.85 Hz, 1H), 7.06 (s, 1H), 4.49 (q, J=7.12 Hz, 2H), 4.41 (d, J=6.44 Hz, 2H), 2.48 (s, 3H), and 1.31 (t, J=7.12 Hz, 3H); MS (ESI) m/e positive ion 344 [M+H]+; negative ion 342 [M−H]−.

Workup

  1. extractionextracted with ethyl acetate (5 mL)
  2. washwashed with H2O (2×5 mL)
  3. concentrationThe organic layer was concentrated in vacuo
  4. custompurified by silica gel chromatography (50-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1550b5baa0c744bb81b11f9749e25703
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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