5,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene → Tartrate

HRID 2180933Notes

Reaction equation

HRID 2180933 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[CH:11]12[CH2:26][CH:22]([CH2:23][NH:24][CH2:25]1)[C:21]1[CH:20]=[C:19]3[C:14]([N:15]=[CH:16][CH:17]=[N:18]3)=[CH:13][C:12]2=1>CO>[C:6]([C@@H:4]([C@H:2]([C:1]([O-:10])=[O:9])[OH:3])[OH:5])([O-:8])=[O:7].[CH:22]12[CH2:26][CH:11]([CH2:25][NH:24][CH2:23]1)[C:12]1[CH:13]=[C:14]3[C:19]([N:18]=[CH:17][CH:16]=[N:15]3)=[CH:20][C:21]2=1

Participants

5

Reactant 2

HCID 1703615,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene2×HCID 444305L-Tartaric acid2×

Product 2

HCID 119400TartrateHCID 1703615,8,14-Triazatetracyclo[10.3.1.02,11.04,9]hexadeca-2,4,6,8,10-pentaene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

One optimized procedure for making the anhydrous Form B comprises charging a speck-free vessel with between 1.1 and 2.2 equivalents of L-tartaric acid and methanol (4 to 50 volumes), and stirring this mixture until dissolved and speck-free filtering the resulting solution into a crystallization vessel. 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene free base (1.0 equivalents) and methanol (4 to 50 volumes) are stirred in a vessel until dissolved at 0 to 50° C., more preferably at 20 to 25° C. The resulting solution of 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene free base is then added over about a period of time ranging from 1 minute to 2 hours, more preferably over about 30 minutes, to the L-tartaric acid solution. The product was allowed to stir at 0 to 40° C., more preferably at 20 to 25° C., for between 1 and 48 hours, more preferably for about 1 hour, and then isolated by filtration. The product is dried generally under vacuum at 20 to 60° C., more preferably at 35 to 45° C., to give Form B of the L-tartrate salt of 5,8,14-triazatetracyclo[10.3.1.02,11.04,9]-hexadeca-2(11),3,5,7,9-pentaene.

Workup

  1. dissolutionuntil dissolved
  2. dissolutionuntil dissolved at 0 to 50° C., more preferably at 20 to 25° C
  3. stirringto stir at 0 to 40° C., more preferably at 20 to 25° C., for between 1 and 48 hours, more preferably for about 1 hour
  4. customisolated by filtration
  5. customThe product is dried generally under vacuum at 20 to 60° C., more preferably at 35 to 45° C.

Sources & evidence

ORD record
ord-2273392accf64f0dbfe6ce14c6ed882d
Source dataset
uspto-grants-2005_05
Patent number
US06890927B2

Reaction notes

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