1-Hydroxybenzotriazole → HCID 178430552, compound

HRID 251031Notes

Reaction equation

HRID 251031 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:28][C:29]2[C:34]([CH:35]([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]([CH2:11][CH2:12][C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)[CH2:28][C:29]2[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][N:30]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 757711-HydroxybenzotriazoleHCID 67272747(3,5-dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine

Product 1

HCID 178430552HCID 178430552, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3,5-dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine (99.1 mg, 0.19 mmol) in anhydrous MeOH (1.5 mL) was added HOBT (108.5 mg, 0.803 mmol) and the resulting mixture was stirred overnight. The mixture was concentrated and purified by radial chromatography on silica gel (1 mm plate; using 6% MeOH/CH2Cl2, followed by CH2Cl2/MeOH/NH4OH; 17:1:1) to afford COMPOUND 176 as a light brown oil (43.4 mg, 62%). 1H NMR (CDCl3) δ 1.00 (d, 6H, J=9.0 Hz), 2.07 (s, 3H), 2.21 (s, 3H), 2.86 (s, 4H), 3.09 (qnt, 1H, J=6.0 Hz), 3.77 (s, 2H), 3.84 (s, 2H), 6.70 (s, 1H), 7.11 (m, 2H), 7.43 (d, 1H, J=7.8 Hz), 7.57 (s, 1H), 8.14 (s, 1H), 8.32 (d, 1H, J=4.7 Hz). 13C NMR (CDCl3) δ 18.2, 18.3, 23.0, 23.5, 27.8, 54.8, 57.6, 58.2, 123.0, 124.4, 130.4, 132.0, 132.6, 133.6, 134.9, 139.1, 143.6, 145.8 146.3, 153.9, 155.7. ES-MS m/z 364 [M+H]+. Anal. Calcd. for C22H29N5.0.6H2O.0.1 CH2Cl2: C, 72.69; H, 8.04; N, 19.27. Found: C, 69.46; H, 8.11; N, 18.24.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by radial chromatography on silica gel (1 mm plate; using 6% MeOH/CH2Cl2, followed by CH2Cl2/MeOH/NH4OH; 17:1:1)

Sources & evidence

ORD record
ord-ca3507adb986494fb9047ef2390ac0e5
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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