Water → HCID 136262690, compound

HRID 706790Notes

Reaction equation

HRID 706790 reaction equation
[OH:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:16][C:15](=[O:17])[C:14]3=[CH:18][CH:19]=[CH:20][N:13]3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[OH2:21].[C:22]1([CH3:32])C=CC(S(O)(=O)=O)=CC=1.O>C(O)CO>[OH:21][CH2:22][CH2:32][O:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:16][C:15](=[O:17])[C:14]3=[CH:18][CH:19]=[CH:20][N:13]3[N:12]=2)=[CH:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 136262675HCID 136262675, compound

Product 1

HCID 136262690HCID 136262690, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a suspension of 2-[4-(1-hydroxy-1-methyl-ethyl)-phenyl]-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (53.9 mg, 0.20 mmol) in ethane-1,2-diol (0.7 ml) is added toluene-4-sulfonic acid monohydrate (3.8 mg, 20 μmol). The reaction mixture is stirred for 7 days at ambient temperature. Water is added to the reaction mixture. The resulting precipitate is filtered off, washed with water and dried under vacuum. It is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 2-{4-[1-(2-hydroxy-ethoxy)-1-methyl-ethyl]-phenyl}-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one as white crystals; HPLC/MS 2.18 min (B), [M+H] 314;

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with water
  3. customdried under vacuum
  4. customIt is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-6d22990755534f29b97f1655d3684566
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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