4-Amino-1-butanol → HCID 78426825, compound

HRID 2205198Notes

Reaction equation

HRID 2205198 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38]>CS(C)=O.O>[C:11]1([C:8]2[N:6]3[N:7]=[C:2]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38])[CH:3]=[CH:4][C:5]3=[N:10][CH:9]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 258684-Amino-1-butanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 90388256HCID 90388256, compound

Product 1

HCID 78426825HCID 78426825, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-chloro-3-(naphthalen-1-yl)imidazo[1,2-b]pyridazine (50 mg, 0.179 mmol, 1.0 equiv) in DMSO (2.0 mL) was added p-toluene sulfonic acid monohydrate (35 mg, 0.184 mmol, 1.0 equiv) and 4-aminobutan-1-ol (200 mg, 2.24 mmol, 12.5 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 30 mg of a white solid, 50%.

Workup

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

Sources & evidence

ORD record
ord-8f1b5f8ce85b4ce09968057a02132e50
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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