Triethylamine → (S)-1-(1-(4-Methoxybenzyl)-1H-indazol-6-yl)ethane-1,2-diyl dimethanesulfonate

HRID 1410341Notes

Reaction equation

HRID 1410341 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:27]=[CH:26][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C@H:22]([OH:25])[CH2:23][OH:24])[CH:20]=3)[CH:15]=[N:14]2)=[CH:10][CH:9]=1.CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([O:25][C@@H:22]([C:19]1[CH:20]=[C:21]2[C:16]([CH:15]=[N:14][N:13]2[CH2:12][C:11]2[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[CH:27][CH:26]=2)=[CH:17][CH:18]=1)[CH2:23][O:24][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67459202(S)-1-(1-(4-Methoxybenzyl)-1H-indazol-6-yl)ethane-1,2-diol

Product 1

HCID 86681513(S)-1-(1-(4-Methoxybenzyl)-1H-indazol-6-yl)ethane-1,2-diyl dimethanesulfonateYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.88 mL, 11.3 mmol) was added dropwise to a solution of (S)-1-(1-(4-methoxybenzyl)-1H-indazol-6-yl)ethane-1,2-diol (1.68 g, 5.63 mmol), Et3N (2.0 mL, 14.1 mmol) and CH2Cl2 (30 mL) at 0° C. After 1 h diluted with CH2Cl2 (100 mL) and washed with 0.5 M HCl, saturated aqueous NaHCO3, brine, and then dried over MgSO4. After the solvent was removed, purification using Biotage Isolera (silica gel, 50-66% EtOAc in hexane) gave the title compound as a sticky white solid (2.13 g, 83%); 1H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.78 (d, J=8.4 Hz, 1H), 7.42 (s, 1H), 7.18-7.12 (m, 3H), 6.82 (d, J=8.5 Hz, 2H), 5.90-5.87 (m, 1H), 5.59-5.50 (m, 2H), 4.55-4.50 (m, 1H), 4.42-4.38 (m, 1H), 3.76 (s, 3H), 3.04 (s, 3H), 2.77 (s, 3H); MS ESI 455.1 [M+H]+, calcd for [C19H22N2O7S2+H]+ 455.1.

Workup

  1. washwashed with 0.5 M HCl, saturated aqueous NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. customAfter the solvent was removed
  4. custompurification

Sources & evidence

ORD record
ord-4eaf0ba8f0714ca995a118d513787eb5
Source dataset
uspto-grants-2014_12
Patent number
US08921545B2

Reaction notes

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