Fumaric Acid → HCID 131729117, compound

HRID 1675691Notes

Reaction equation

HRID 1675691 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])/[CH:47]=[CH:48]/[C:49]([OH:51])=[O:50]>C(O)(C)C>[C:46]([OH:53])(=[O:52])/[CH:47]=[CH: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 444972Fumaric AcidHCID 23729488HCID 23729488, compound

Product 1

HCID 131729117HCID 131729117, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

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”, 100 mg, about 0.161 mmol, as a substantially amorphous form thereof, as prepared in Example 1B (alternative preparation no. 2)] was dissolved in isopropanol (1 ml) at room temperature. The resulting solution was added to fumaric acid (18.7 mg±1 mg, 1 equivalent) and heated to 40° C. The reaction mixture was left to temperature cycle between 0° C. and 40° C. overnight. The next day, the reaction mixture was a slurry, and the solid from this was isolated by filtration, washed with isopropanol (0.5 ml) and dried at ambient temperature under vacuum overnight. 54.4 mg of dried solid was obtained. NMR data appears to support a stoichiometry consistent with the solid product being substantially a hemifumarate salt.

Workup

  1. customthe solid from this was isolated by filtration
  2. washwashed with isopropanol (0.5 ml)
  3. customdried at ambient temperature under vacuum overnight

Sources & evidence

ORD record
ord-be945017e57e40e2af3b4c2aa6fedcb1
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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