p-Toluenesulfonic acid monohydrate → HCID 178521580, compound

HRID 2205229Notes

Reaction equation

HRID 2205229 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:19][C:14]4=[N:15][CH:16]=[CH:17][CH:18]=[C:13]4[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:32][C@H:33]1[CH2:38][CH2:37][C@H:36]([OH:39])[CH2:35][CH2:34]1>CS(C)=O.O>[S:19]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH:12]=[C:11]1[C:8]1[N:6]2[N:7]=[C:2]([NH:32][C@H:33]3[CH2:38][CH2:37][C@H:36]([OH:39])[CH2:35][CH2:34]3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 90388516HCID 90388516, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178521580HCID 178521580, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-3-(thieno[2,3-b]pyridin-2-yl)imidazo[1,2-b]pyridazine (45 mg, 0.157 mmol, 1.0 equiv) in DMSO (2.0 mL) was added p-toluene sulfonic acid monohydrate (22 mg, 0.157 mmol, 1.0 equiv) and trans-4-aminocyclohexanol (0.784 mmol, 5.0 equiv) and heated to 100° C. for 24 h. The reaction mixture was diluted with water and extracted with ethyl acetate. Purification by column chromatography using 5% methanol in dichloromethane elution gave 40 mg of the yellow solid, 70%.

Workup

  1. extractionextracted with ethyl acetate
  2. customPurification by column chromatography
  3. wash5% methanol in dichloromethane elution

Sources & evidence

ORD record
ord-f10a358f225442af8257e593fc503f9e
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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