p-Toluenesulfonic acid monohydrate → HCID 178423681, compound

HRID 2205208Notes

Reaction equation

HRID 2205208 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[N:6][N:5]2[C:10]=1[C:11]1[S:15][C:14]2[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:13]=2[CH:12]=1.O.C1(C)C=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.O>[CH3:20][C:16]1[C:14]2[S:15][C:11]([C:10]3[N:5]4[N:6]=[C:7]([NH:33][C@H:34]5[CH2:39][CH2:38][C@H:37]([OH:40])[CH2:36][CH2:35]5)[CH:8]=[CH:9][C:4]4=[N:3][CH:2]=3)=[CH:12][C:13]=2[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 90388658HCID 90388658, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178423681HCID 178423681, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of -chloro-3-(7-methylbenzo[b]thiophen-2-yl)imidazo[1,2-b]pyridazine (50 mg, 0.168 mmol, 1.0 equiv) in DMSO (2.0 mL) was added p-toluene sulfonic acid monohydrate (23 mg, 0.168 mmol, 1.0 equiv) and trans-4-aminocyclohexanol (0.840 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 32 mg of the yellow solid, 48%.

Workup

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

Sources & evidence

ORD record
ord-a0fb79101f7345af99fb039907eec31a
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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