4,5,6,7-Tetrahydro-N6-propyl-2,6-benzothiazolediamine → Dexpramipexole

HRID 1897741

Reaction equation

HRID 1897741 reaction equation
NC1SC2C[C@@H](N)CCC=2N=1.[CH2:12]([NH:15][C@H:16]1[CH2:25][CH2:24][C:19]2[N:20]=[C:21]([NH2:23])[S:22][C:18]=2[CH2:17]1)[CH2:13][CH3:14].NC1SC2CC(NCCC)CCC=2N=1>>[CH2:12]([NH:15][C@@H:16]1[CH2:25][CH2:24][C:19]2[N:20]=[C:21]([NH2:23])[S:22][C:18]=2[CH2:17]1)[CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 48854,5,6,7-Tetrahydro-N6-propyl-2,6-benzothiazolediamineHCID 119570PramipexoleHCID 115211532,6-Diamino-4,5,6,7-tetrahydrobenzothiazole, (S)-

Product 1

HCID 59868Dexpramipexole

Procedure

The products of purification processes were then analyzed by HPLC for chemical and chiral purity. FIG. 3A shows an exemplary HPLC trace starting material. In FIG. 4A, a large (6R)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine peak can be observed at about 6 minutes and a much smaller (6S)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine peak can be seen at about 9 minutes. The area of these peaks provides an estimated composition for the mixture which is shown in the table below the trace, and shows the mixture as containing about 90.2% (6R) and 8.8% (6S)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine. FIG. 3B shows an exemplary trace of the 2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole product following purification. In FIG. 3B, a large (6R)2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole peak is observed at about 6 minutes, and no (6S)2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole peak is observed. It is additionally of note that several other minor peaks are also reduced or eliminated in the product trace, and the table below the trace indicates that (6R)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine makes up 99.9% of the product solution which is within the limits of analytical detectability. Results for each exemplary reaction are provided in Table 3:

Workup

  1. customThe products of purification processes
  2. waita much smaller (6S)-4,5,6,7-tetrahydro-N6-propyl-2,6-benzothiazole-diamine peak can be seen at about 9 minutes
  3. customThe area of these peaks provides an estimated composition for the mixture which
  4. custompurification
  5. waitIn FIG. 3B, a large (6R)2-amino-4,5,6,7-tetrahydro-6-(propylamino)benzothiazole peak is observed at about 6 minutes
  6. customResults for each exemplary reaction
  7. customare provided in Table 3

Sources & evidence

ORD record
ord-c248e6b2a55240bd96b9daae946884b5
Source dataset
uspto-grants-2013_08
Patent number
US08519148B2

Linked notes

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