Triethylamine → HCID 71509771, compound

HRID 1404211Notes

Reaction equation

HRID 1404211 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([S:8](Cl)(=[O:10])=[O:9])[C:4]([CH3:12])=[N:3]1.[C:13]1([CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29][C:30]4[S:31][C:32]([CH2:35][NH2:36])=[CH:33][N:34]=4)[CH:25]=3)[O:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>O1CCCC1>[C:13]1([CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:29][C:30]4[S:31][C:32]([CH2:35][NH:36][S:8]([C:5]5[C:4]([CH3:12])=[N:3][N:2]([CH3:1])[C:6]=5[CH3:7])(=[O:10])=[O:9])=[CH:33][N:34]=4)[CH:25]=3)[O:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27373401,3,5-trimethyl-1H-pyrazole-4-sulfonyl chlorideHCID 71292725HCID 71292725, compound

Product 1

HCID 71509771HCID 71509771, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

33 mg of 1,3,5-trimethyl-1H-pyrazole-4-sulfonic acid chloride (0.16 mmol, 1.2 eq) were weighted into a reaction tube and dissolved in dry tetrahydrofuran (1 ml). 44 mg of [2-(2-phenyl-chroman-6-yloxy)-thiazol-5-ylmethyl]amine (0.13 mmol) in dry tetrahydrofuran (3 ml) and 30 mg triethylamine (0.3 mmol, 2.3 eq) were added, the tube was flushed with argon, closed with a screw cap, and shaken over night at 40° C. 0.008 ml of tris-(2-aminoethyl)amine in 0.5 ml tetrahydrofuran were added, the mixture was shaken for 2 h at room temperature and then evaporated. The residue was dissolved in 2 ml of a mixture of dimethylformamide/trifluoroacetic acid (19:1), filtered, and submitted to preparative reversed phase HPLC purification (water/acetonitrile gradient (+0.1% trifluoroacetic acid)). 1,3,5-Trimethyl-1H-pyrazole-4-sulfonic acid [2-(2-phenyl-chroman-6-yloxy)-thiazol-5-ylmethyl]-amide was obtained as a white solid (42 mg, 63%).

Workup

  1. customthe tube was flushed with argon
  2. customclosed with a screw
  3. customcap
  4. addition0.008 ml of tris-(2-aminoethyl)amine in 0.5 ml tetrahydrofuran were added
  5. stirringthe mixture was shaken for 2 h at room temperature
  6. customevaporated
  7. dissolutionThe residue was dissolved in 2 ml of a mixture of dimethylformamide/trifluoroacetic acid (19:1)
  8. filtrationfiltered
  9. customphase HPLC purification (water/acetonitrile gradient (+0.1% trifluoroacetic acid))

Sources & evidence

ORD record
ord-90ecf2a9d2684f068607c19b7e3e36fa
Source dataset
uspto-grants-2014_12
Patent number
US08912224B2

Reaction notes

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