Phosphoric Acid → HCID 67076828, compound

HRID 1675692Notes

Reaction equation

HRID 1675692 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].[P:46](=[O:50])([OH:49])([OH:48])[OH:47]>C(C(C)=O)C(C)C.O>[P:46]([OH:50])([OH:49])([OH:48])=[O:47].[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]

Participants

5

Reactant 2

HCID 1004Phosphoric Acid2×HCID 23729488HCID 23729488, compound

Product 1

HCID 67076828HCID 67076828, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent2×

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 suspended in methyl isobutyl ketone (MIBK, 1 ml), producing a slightly turbid solution. Phosphoric acid (H3PO4, 85 wt % solution in water (commercially available e.g. from Aldrich), 7.9 microliters, 1 equivalent) was added. Methyl isobutyl ketone (MIBK, 0.5 ml) was added. A gum appeared at the bottom of the vial, which was left to temperature cycle between 0° C. and 40° C. for about 2 days. A suspension had formed, and from this the resulting solid was isolated by filtration, washed with isopropanol (0.5 ml) and dried at 40° C. under vacuum overnight. 74.4 mg of dried solid was obtained.

Workup

  1. customproducing a slightly turbid solution
  2. customA suspension had formed
  3. customfrom this the resulting solid was isolated by filtration
  4. washwashed with isopropanol (0.5 ml)
  5. customdried at 40° C. under vacuum overnight

Sources & evidence

ORD record
ord-aff41a43e4404a5cbd9bd8bff2394900
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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