Dimethylamine → HCID 178483202, compound

HRID 2401989Notes

Reaction equation

HRID 2401989 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[S:12][C:11]=2[C:21]2[NH:25][CH:24]=[N:23][N:22]=2)O)=[CH:4][CH:3]=1.[N:26]1[CH:31]=CC=C[CH:27]=1.CS(Cl)(=O)=O.CNC>C(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[S:12][C:11]=2[C:21]2[NH:25][CH:24]=[N:23][N:22]=2)[N:26]([CH3:31])[CH3:27])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178519583HCID 178519583, compound

Product 1

HCID 178483202HCID 178483202, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (4-chlorophenyl)[5-pyridin-4-yl-2-(4H-1,2,4-triazol-3-yl)-3-thienyl]methanol (141 mg, 0.382 mmol) (synthesized in an analogous way as described in Example 3) in methylene chloride (2.8 mL) was added pyridine (6.0 mL, 74 mmol) and methanesulfonyl chloride (0.148 mL, 1.91 mmol) at 0° C. After the addition, the mixture was warmed to rt and stirred for 30 min and then heated at 60° C. for 20 min. The mixture was cooled in an ice bath and dimethylamine (0.553 mL, 11.5 mmol) in THF was added to the mixture. After the addition, the ice bath was removed and the mixture was stirred at rt for 30 min and then heated at 55° C. for 2 h. The mixture was cooled, concentrated, and the residue was purified by HPLC to afford 1-(4-chlorophenyl)-N,N-dimethyl-1-[5-pyridin-4-yl-2-(4H-1,2,4-triazol-3-yl)-3-thienyl]methanamine as white powder (115 mg, 76%). LCMS: (AA) ES+ 396.3, 398.1; 1H NMR (400 MHz, d6-DMSO) δ: 14.48-14.27 (m, 1H), 8.71 (s, 1H), 8.57 (dd, J=4.55, 1.62 Hz, 2H), 7.95 (s, 1H), 7.73-7.63 (m, 4H), 7.39-7.30 (m, 2H), 5.53 (s, 1H), 2.13 (s, 6H).

Workup

  1. customsynthesized in an analogous way
  2. additionAfter the addition
  3. temperatureheated at 60° C. for 20 min
  4. temperatureThe mixture was cooled in an ice bath
  5. additionAfter the addition
  6. customthe ice bath was removed
  7. stirringthe mixture was stirred at rt for 30 min
  8. temperatureheated at 55° C. for 2 h
  9. temperatureThe mixture was cooled
  10. concentrationconcentrated
  11. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-fd8e766c6abd4368a397e83eb090f1df
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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