Triethylamine → HCID 86668348, compound

HRID 1189527Notes

Reaction equation

HRID 1189527 reaction equation
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[C:24](=[S:34])(Cl)[O:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1.C(N(CC)CC)C>C1COCC1>[F:23][C:2]([F:1])([F:22])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:21]=[CH:20][C:18]([NH:19][C:24](=[S:34])[O:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 50453324-Fluorophenyl chlorothionoformateHCID 578244904-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline

Product 1

HCID 86668348HCID 86668348, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 25 mL round-bottomed flask were added 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline (200 mg, 0.624 mmol), O-4-fluorophenyl carbonochloridothioate (238 mg, 1.249 mmol), and triethylamine (0.348 mL, 2.498 mmol) in THF (5 mL). The solution was stirred under ambient conditions for 2 h before the solvent was removed under reduced pressure. The crude product was added to a silica gel column and was eluted with EtOAc/hexanes gradient to afford the title compound (50 mg, 0.105 mmol, 17%) as a yellow solid: mp 164-169° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.42 (s, 1H), 8.19-8.04 (m, 6H), 7.97 (br s, 1H), 7.66-7.57 (d, J=8.24 Hz, 2H), 7.33-7.19 (m, 4H); ESIMS m/z 475 (M+1).

Workup

  1. customwas removed under reduced pressure
  2. additionThe crude product was added to a silica gel column
  3. washwas eluted with EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-19c0bf933c524fa082e74f816275c17c
Source dataset
uspto-grants-2014_03
Patent number
US08674109B2

Reaction notes

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