L-Tartaric acid → 1-Methyl-1H-pyrazole-4-sulfonic acid {2-[3'-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide L-tartrate

HRID 553511Notes

Reaction equation

HRID 553511 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][N:24]([CH3:34])[S:25]([C:28]4[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=4)(=[O:27])=[O:26])[CH2:18][CH2:17]3)=[N:12][CH:13]=[CH:14][N:15]=2)=[CH:6][CH:5]=1.[C:35]([OH:44])(=[O:43])[C@@H:36]([C@H:38]([C:40]([OH:42])=[O:41])[OH:39])[OH:37]>CCO>[C:40]([C@@H:38]([C@H:36]([C:35]([OH:44])=[O:43])[OH:37])[OH:39])([OH:42])=[O:41].[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([N:16]3[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][N:24]([CH3:34])[S:25]([C:28]4[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=4)(=[O:26])=[O:27])[CH2:20][CH2:21]3)=[N:12][CH:13]=[CH:14][N:15]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 251833521-methyl-1H-pyrazole-4-sulfonic acid {2-[3'-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide

Product 1

HCID 673666331-Methyl-1H-pyrazole-4-sulfonic acid {2-[3'-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-yl]-ethyl}-methyl-amide L-tartrate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

1-Methyl-1H-pyrazole-4-sulfonic acid {2-[3′-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-amide (1.0 equivalents) and L-tartaric acid (0.95 equivalents) is suspended in 2B3 EtOH (10 volumes) and heated to at least 75° C. for at least 60 min. The resulting slurry is then cooled to 20° C. over at least 90 min. After granulating at 20° C. for at least 60 min., the resulting solids are filtered and washed with 2B3 EtOH (2×3 volumes). The cake is then dried at 50° C. under vacuum with nitrogen bleed for at least 12 hr. 1-Methyl-1H-pyrazole-4-sulfonic acid {2-[3′-(4-methoxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-yl]-ethyl}-methyl-amide L-tartrate is isolated as an off-white solid (92% yield). m.p. 161° C.

Workup

  1. temperatureheated to at least 75° C. for at least 60 min
  2. waitAfter granulating at 20° C. for at least 60 min.
  3. filtrationthe resulting solids are filtered
  4. washwashed with 2B3 EtOH (2×3 volumes)
  5. customThe cake is then dried at 50° C. under vacuum with nitrogen
  6. waitbleed for at least 12 hr

Sources & evidence

ORD record
ord-7baed80ee61549b08d5e0dcc8e28f044
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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