Ethyl isocyanate → HCID 86620396, compound

HRID 252720Notes

Reaction equation

HRID 252720 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[NH2:6][C:7]1[S:8][C:9]([C:13]2[CH:14]=[C:15]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:16]([Cl:19])=[N:17][CH:18]=2)=[C:10]([CH3:12])[N:11]=1>C1COCC1>[Cl:19][C:16]1[C:15]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:14][C:13]([C:9]2[S:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[N:11][C:10]=2[CH3:12])=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 86620384HCID 86620384, compound

Product 1

HCID 86620396HCID 86620396, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
125 °C

Procedure

Ethyl isocyanate (0.036 mL) was added to a stirred solution of N-[5-(2-amino-4-methyl-1,3-thiazol-5-yl)-2-chloropyridin-3-yl]methanesulfonamide (48 mg) in THF (0.5 mL) and the mixture was placed in a sealed glass reaction vessel and heated to 125° C. in a microwave reactor for 1 hour. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using a solvent gradient of 0% to 6% methanol in dichloromethane as eluent. The material so obtained was purified further by preparative HPLC on reversed-phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained the title compound as a solid (16 mg); 1H NMR Spectrum: (DMSOd6) 1.07 (t, 3H), 2.31 (s, 3H), 3.1, (s, 3H), 3.10-3.20 (m, 2H), 6.54 (br s, 11H), 7.82 (d, 1H), 8.24 (s, 1H), 9.84 (s, 1H), 10.53 (s, 1H); Mass Spectrum: M+H+ 390.

Workup

  1. customthe mixture was placed in a sealed glass reaction vessel
  2. customThe resultant mixture was evaporated
  3. customthe residue was purified by column chromatography on silica using a solvent gradient of 0% to 6% methanol in dichloromethane as eluent
  4. customThe material so obtained
  5. customwas purified further by preparative HPLC on reversed-phase silica using a solvent gradient of 10% to 100% acetonitrile in water (containing 1% acetic acid) as eluent
  6. customThe material so obtained
  7. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-4ba8a6eed2604942a13f74e86c78eeb0
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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