Succinic Acid → HCID 131729116, compound

HRID 1675690Notes

Reaction equation

HRID 1675690 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:44][CH3:45])=[C:10]([CH2:19][NH:20][C:21](=[O:43])[C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:42])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][N:37]([CH2:39][CH2:40][OH:41])[CH3:38])=[CH:24][CH:23]=3)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[C:46]([OH:53])(=[O:52])[CH2:47][CH2:48][C:49]([OH:51])=[O:50]>C(O)(C)C>[C:46]([OH:53])(=[O:52])[CH2:47][CH2:48][C:49]([OH:51])=[O:50].[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:44][CH3:45])=[C:10]([CH2:19][NH:20][C:21](=[O:43])[C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:42])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][N:37]([CH2:39][CH2:40][OH:41])[CH3:38])=[CH:24][CH:23]=3)[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:44][CH3:45])=[C:10]([CH2:19][NH:20][C:21](=[O:43])[C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:42])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][N:37]([CH3:38])[CH2:39][CH2:40][OH:41])=[CH:24][CH:23]=3)[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 23729488HCID 23729488, compound

Product 1

HCID 131729116HCID 131729116, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Isopropanol (10 ml) was added to N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-4-({8-[(2-hydroxyethyl)(methyl)amino]octanoyl}amino)benzamide (the “free base”, 1 g, e.g. which can be as prepared in Example 1B) and the mixture was heated at 60° C. for 0.5 hour to dissolve the free base. A solution of succinic acid (199 mg, 1.05 equiv.) in isopropanol (2 ml) was added to the solution of the free base, and the mixture was left to temperature cycle between 0° C. and 40° C. for about 3 days. The resulting solid was isolated by filtration, washed with isopropanol (about 2 ml), left on the filter paper for a while, and dried under vacuum at 40° C. in an oven overnight to give the title compound (0.833 g). NMR appeared to show approximately 1:0.471 stoichiometry of free base: succinate, and some isopropanol present (e.g. approximately 0.73% w/w). XRPD appeared to suggest the product was mainly crystalline material.

Workup

  1. customas prepared in Example 1B) and the mixture
  2. dissolutionto dissolve the free base
  3. customThe resulting solid was isolated by filtration
  4. washwashed with isopropanol (about 2 ml)
  5. waitleft on the filter paper for a while
  6. customdried under vacuum at 40° C. in an oven overnight

Sources & evidence

ORD record
ord-b4d6f7f527f84ee98ff45bd94ab9d43d
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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