p-Toluenesulfonic acid → HCID 178430604, compound

HRID 2205226Notes

Reaction equation

HRID 2205226 reaction equation
[S:1]1[C:5]([C:6]2[N:10]3[N:11]=[C:12](Cl)[C:13]([CH3:16])=[C:14]([CH3:15])[C:9]3=[N:8][CH:7]=2)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2.CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:33][C@H:34]1[CH2:39][CH2:38][C@H:37]([OH:40])[CH2:36][CH2:35]1>CS(C)=O>[S:1]1[C:5]([C:6]2[N:10]3[N:11]=[C:12]([NH:33][C@H:34]4[CH2:39][CH2:38][C@H:37]([OH:40])[CH2:36][CH2:35]4)[C:13]([CH3:16])=[C:14]([CH3:15])[C:9]3=[N:8][CH:7]=2)=[CH:4][C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]1=2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 90387518HCID 90387518, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178430604HCID 178430604, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(benzo[b]thiophen-2-yl)-6-chloro-7,8-dimethylimidazo[1,2-b]pyridazine (40 mg, 0.128 mmol, 1.0 equiv) in DMSO (1.00 mL) was added p-TSA (24 mg, 0.128 mmol, 1.0 equiv) and trans-4-aminocyclohexanol (73 mg, 0.638 mmol, 5.0 equiv) and heated to 100° C. for 24 h. Purification by column chromatography using 5% methanol in dichloromethane elution gave 31 mg, 62%.

Workup

  1. customPurification by column chromatography
  2. wash5% methanol in dichloromethane elution
  3. customgave 31 mg, 62%

Sources & evidence

ORD record
ord-89ec133e1f1e48688cc81a8442a3ec9b
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

Loading…