Hydrogen Bromide → HCID 24985646, compound

HRID 1675689Notes

Reaction equation

HRID 1675689 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].[BrH:46]>C(O)(C)C>[BrH:46].[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

4

Reactant 2

HCID 260Hydrogen BromideHCID 23729488HCID 23729488, compound

Product 1

HCID 24985646HCID 24985646, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

Isopropanol (15 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”, 1.5 g, e.g. which can be as prepared in Example 1B) and the mixture was heated at 60° C. for 1 hour to dissolve the free base. 48% Aqueous hydrobromic acid (0.273 ml, 1 equiv.) was added, and the mixture was left to temperature cycle between 0° C. and 40° C. over the weekend (about 3 days). The resulting solid was isolated by filtration, washed with isopropanol (about 5 ml), left on the filter for a while, and then dried under vacuum at 40° C. in a vacuum oven overnight to give the title compound (1.286 g). NMR appeared to show some isopropanol present (e.g. very approx. 0.89% w/w). XRPD appeared to suggest product was partly crystalline material. Ion chromatography of the product appears to confirm that the stoichiometry of the salt is that of a monohydrobromide.

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 5 ml)
  5. waitleft on the
  6. filtrationfilter for a while
  7. customdried under vacuum at 40° C. in a vacuum oven overnight

Sources & evidence

ORD record
ord-178d32aa1cde47af8fd2b66b409f7ca2
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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