Ammonia → HCID 59644548, compound

HRID 2252003Notes

Reaction equation

HRID 2252003 reaction equation
[CH2:1]([C:8]1(S(C2C=CC(C)=CC=2)(=O)=O)[CH:12]([C:13]2[N:14]=[N:15][N:16]([CH2:24][C:25]3[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=3)[C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)O[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:49].CO>C1(C)C(C)=CC=CC=1>[CH2:1]([C:8]1[NH:9][CH:10]=[N:49][C:12]=1[C:13]1[N:14]=[N:15][N:16]([CH2:24][C:25]2[CH:26]=[C:27]([C:35]([F:38])([F:36])[F:37])[CH:28]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:30]=2)[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86601253HCID 86601253, compound

Product 1

HCID 59644548HCID 59644548, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
136 °C

Procedure

Combine 4-[4-benzyl-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazol-5-yl]-1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazole (0.084 mmol), 1.0 mL of xylene, and 7N solution of ammonia in methanol (48.0 μL, 0.337 mmol). Heat in a sealed pyrex tube to 136° C. After 18 hours, cool to RT, and concentrate the mixture to 1.0 mL and apply to a 2 mm chromatotron plate with CH2Cl2 and elute with a EtOAc/hexanes gradient to provide the title compound. Exact Mass 527.2: mass spectrum (IS): m/z=529.1 (M+1), 527.1 (M−1); 1H NMR (250 MHz, CDCl3) 7.84 (s, 1H), 7.67 (s, 1H), 7.65-7.05 (m, 13H), 5.60 (s, 2H), 4.28 (s, 2H).

Workup

  1. temperaturecool to RT
  2. concentrationconcentrate the mixture to 1.0 mL
  3. washapply to a 2 mm chromatotron plate with CH2Cl2 and elute with a EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-c708b183c7664e30bb3e5234bc7c6625
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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