Propyl p-toluenesulfonate → Pramipexole p-toluenesulfonate
Reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:10][C@@H:9]([NH2:11])[CH2:8][CH2:7][C:5]=2[N:6]=1.[S:12]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)([O:15][CH2:16][CH2:17][CH3:18])(=[O:14])=[O:13]>CN(C)C=O>[CH2:16]([NH:11][C@H:9]1[CH2:8][CH2:7][C:5]2[N:6]=[C:2]([NH2:1])[S:3][C:4]=2[CH2:10]1)[CH2:17][CH3:18].[CH3:23][C:22]1[CH:24]=[CH:25][C:19]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:20][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A 1000 ml, three necked flask was equipped with an overhead stirrer, a temperature probe, a heating mantle, a claisen joint, a condenser, and a 250 ml addition funnel. The flask was charged with 25 grams of (6S)-2,6 diamino-4,5,6,7-tetrahydro-benzothiazole, followed by 200 ml of dimethyl formamide (DMF). Under continuous stirring, the mixture was heated to a temperature of 75° C. The addition funnel was charged with a solution of 39.5 grams propyl tosylate and 32.5 ml diisopropylethyleamine in 50 ml DMF. This solution was added to the 1000 ml flask dropwise over a period of 2.0 hours. The reaction was monitored by analysis on HPLC.
Workup
- customA 1000 ml, three necked flask was equipped with an overhead stirrer
- additiona temperature probe, a heating mantle, a claisen joint, a condenser, and a 250 ml addition funnel
- additionThis solution was added to the 1000 ml flask dropwise over a period of 2.0 hours
Sources & evidence
- ORD record
- ord-200a0547bfcd4a279734f32976b9b30b
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08519148B2
Reaction notes
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