Anisole → HCID 57405174, compound

HRID 1520089Notes

Reaction equation

HRID 1520089 reaction equation
COC1C=CC(C[N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:14][CH:15]=3)[C:10]([C:22]3[N:23]=[N:24][N:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([N:35]5[CH2:40][CH2:39][O:38][CH2:37][CH2:36]5)=[O:34])=[CH:29][CH:28]=4)[CH:26]=3)=[N:9]2)=CC=1.C1(OC)C=CC=CC=1>C(O)(C(F)(F)F)=O.O>[N:35]1([C:33]([C:30]2[CH:31]=[CH:32][C:27]([N:25]3[CH:26]=[C:22]([C:10]4[C:11]5[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][OH:21])[CH:12]=5)[NH:8][N:9]=4)[N:23]=[N:24]3)=[CH:28][CH:29]=2)=[O:34])[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1

Participants

5

Reactant 2

HCID 7519AnisoleHCID 67981389HCID 67981389, compound

Product 1

HCID 57405174HCID 57405174, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-[(1-(4-methoxybenzyl)-3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazol-5-yl)oxy]propan-1-ol (43 mg; 0.08 mmol; 1.0 eq.) and anisole (124 mL, 1.13 mmol, 15 eq.) in TFA (2 mL) and water (2.7 mL) was stirred at RT for 48 h. Reaction mixture was concentrated under reduced pressure and purified by preparative HPLC to give the title compound as a brown gum (10.5 mg, 31%). 1H NMR (300 MHz, DMSO-d6) δ 13.25 (s, 1H), 9.35 (s, 1H), 8.15 (d, J=8.6 Hz, 2H), 7.77-7.72 (m, 1H), 7.69 (d, J=8.6 Hz, 2H), 7.52 (d, J=9.0 Hz, 1H), 7.10 (dd, J=9.0, 2.4 Hz, 1H), 4.61 (t, J=5.2 Hz, 1H), 4.21-4.06 (m, 2H), 3.78-3.24 (m, 10H), 2.02-1.82 (m, 2H). HPLC (max plot) 97.2%; Rt %2.63 min. UPLC/MS: (MS+) 449.1, (MS−) 447.1.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-d1461f0497254e4e874959f61c5919cb
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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