p-Toluenesulfonic acid monohydrate → HCID 178521583, compound

HRID 2205234Notes

Reaction equation

HRID 2205234 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:19][C:18]4[C:13](=[N:14][CH:15]=[CH:16][CH:17]=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:18]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=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 90388025HCID 90388025, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178521583HCID 178521583, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-3-(thieno[3,2-b]pyridin-2-yl)imidazo[1,2-b]pyridazine (40 mg, 0.139 mmol, 1.0 equiv) in DMSO (2.0 mL) was added p-toluene sulfonic acid monohydrate (20 mg, 0.139 mmol, 1.0 equiv) and trans-4-aminocyclohexanol (0.695 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, 79%.

Workup

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

Sources & evidence

ORD record
ord-a7517d9777e14133a18ef1f9f1ba3f99
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

Loading…