Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 86618944, compound

HRID 1675694Notes

Reaction equation

HRID 1675694 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]12([CH2:56][S:57]([OH:60])(=[O:59])=[O:58])[C:53]([CH3:55])([CH3:54])[CH:50]([CH2:51][CH2:52]1)[CH2:49][C:47]2=[O:48]>C(C(C)=O)C(C)C>[C:46]12([CH2:56][S:57]([OH:60])(=[O:58])=[O:59])[C:53]([CH3:55])([CH3:54])[CH:50]([CH2:51][CH2:52]1)[CH2:49][C:47]2=[O:48].[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 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 23729488HCID 23729488, compound

Product 1

HCID 86618944HCID 86618944, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

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)] and (+)-camphorsulfonic acid (37.4 mg±1 mg, 1 equivalent) were suspended in methyl isobutyl ketone (MIBK, 5 ml). The resulting solution/suspension was left to temperature cycle between 0° C. and 40° C. overnight. The next day, a suspension had formed, and from this the resulting solid was isolated by filtration, washed with methyl isobutyl ketone (MIBK, 1 ml) and dried at 40° C. under vacuum overnight. 111.4 mg of dried solid was obtained. NMR data appears to support a stoichiometry consistent with the solid product being substantially a mono-(+)-camphorsulfonate.

Workup

  1. customThe next day, a suspension had formed
  2. customfrom this the resulting solid was isolated by filtration
  3. washwashed with methyl isobutyl ketone (MIBK, 1 ml)
  4. customdried at 40° C. under vacuum overnight

Sources & evidence

ORD record
ord-d435a684e5cf42b7895f8d8cdc5b2366
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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