1-Hydroxybenzotriazole → HCID 178430551, compound

HRID 251029Notes

Reaction equation

HRID 251029 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:28][C:29]2[C:34]([C:35]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:11][CH2:12][C:13]2[N:14]=[CH:15][N:16](S(C3C=CC(C)=CC=3)(=O)=O)[CH:17]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.C1C=CC2N(O)N=NC=2C=1>CO>[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:28][C:29]2[C:34]([C:35]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:11][CH2:12][C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 757711-HydroxybenzotriazoleHCID 67272433(3,5-dimethyl-pyridin-2-ylmethyl)-{3-[1-(4-fluoro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl}-{2-[1-{toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine

Product 1

HCID 178430551HCID 178430551, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3,5-dimethyl-pyridin-2-ylmethyl)-{3-[1-(4-fluoro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl}-{2-[1-{toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine (87.3 mg, 0.143 mmol) in anhydrous MeOH (1.5 mL) was added HOBT (77.1 mg, 0.57 mmol). After stirring overnight the reaction mixture was concentrated. Purification by radial chromatography on silica gel using 5% MeOH/CH2Cl2 afforded COMPOUND 175 (36 mg, 55%) as a clear oil. 1H NMR (CDCl3) δ 1.65 (s, 6H), 1.97 (s, 3H), 2.20 (s, 3H), 2.53 (s, 4H), 3.30 (s, 2H), 3.37 (s, 2H), 6.63 (s, 1H), 6.88 (t, 2H, J=8.52 Hz), 7.04 (m, 3H), 7.30 (m, 1H), 7.61 (s, 1H), 7.93 (d, 1H, J=7.91 Hz), 8.05 (s, 1H), 8.55 (d, 1H, J=3.58 Hz). 13C NMR (CDCl3) δ 18.1, 18.2, 22.8, 31.4, 42.4, 53.3, 57.8, 58.8, 115.5, 115.8, 122.4, 124.1, 127.5, 127.6, 130.2, 132.1, 132.6, 134.5, 134.7, 139.2, 144.0, 145.4, 146.4, 146.5, 153.4, 158.5, 159.8. ES-MS m/z 458 [M+H]+. Anal. Calcd. for C28H32FN5.1.1H2O.0.3 CH2Cl2: C, 73.49; H, 7.05; N, 15.30. Found: C, 70.02; H, 7.02; N, 14.87.

Workup

  1. concentrationwas concentrated
  2. customPurification by radial chromatography on silica gel using 5% MeOH/CH2Cl2 afforded COMPOUND 175 (36 mg, 55%) as a clear oil

Sources & evidence

ORD record
ord-6332154e6de94d2ea3f45a6605cc89c5
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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