Methanol → HCID 59644545, compound

HRID 2252004Notes

Reaction equation

HRID 2252004 reaction equation
[F:1][C:2]([F:49])([F:48])[C:3]1[CH:4]=[C:5]([CH:41]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:43]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([CH:18]2O[CH:21]=[N:20][C:19]2([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])S(C2C=CC(C)=CC=2)(=O)=O)[N:9]=[N:8]1.C[NH2:51].CO>C1(C)C(C)=CC=CC=1>[F:47][C:44]([F:46])([F:45])[C:42]1[CH:41]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:49])[F:48])[CH:43]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[N:51]=[CH:21][NH:20][C:19]=2[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:40])[N:9]=[N:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 86601254HCID 86601254, compound

Product 1

HCID 59644545HCID 59644545, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Combine 1-(3,5-bis-trifluoromethyl-benzyl)-4-[4-(2-chloro-benzyl)-4-(toluene-4-sulfonyl)-4,5-dihydro-oxazol-5-yl]-5-phenyl-1H-[1,2,3]triazole (0.100 mmol), 2.5 mL of xylene, and 2N solution of methylamine in methanol (0.2 mL, 0.40 mmol) and heat in a sealed pyrex tube to 135° C. After 19 hours, cool to RT. Concentrate the mixture to 1.0 mL and apply to a 2 mm chromatotron plate with CH2Cl2 and EtOAc and elute with a 100 mL of Hexanes, and 200 mL each of 20:80 EtOAc/Hexanes, 30:70 EtOAc/Hexanes, 50:50 Hexanes/EtOAc, 85:15 EtOAc/Hexanes to provide the title compound: Exact Mass 561.1: mass spectrum (IS): m/z=563.1 (M+1), 561.1 (M−1); 1H NMR (250 MHz, CDCl3) 7.74 (s, 1H), 7.62 (s, 1H), 7.48-7.32 (m, 6H), 7.30-7.00 (m, 6H), 5.52 (s, 2H), 4.20 (s, 2H).

Workup

  1. concentrationConcentrate the mixture to 1.0 mL
  2. washapply to a 2 mm chromatotron plate with CH2Cl2 and EtOAc and elute with a 100 mL of Hexanes, and 200 mL each of 20:80 EtOAc/Hexanes, 30:70 EtOAc/Hexanes, 50:50 Hexanes/EtOAc, 85:15 EtOAc/Hexanes

Sources & evidence

ORD record
ord-98cbd23df2084f768a9633612d504990
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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