p-Toluenesulfonic acid monohydrate → Ipatasertib tosylate

HRID 628815Notes

Reaction equation

HRID 628815 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH2:28][NH:29][CH:30]([CH3:32])[CH3:31])[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:18]4[C@H:25]([CH3:26])[CH2:24][C@@H:23]([OH:27])[C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.O.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(#N)C>[C:34]1([CH3:44])[CH:35]=[CH:36][C:37]([S:40]([OH:43])(=[O:41])=[O:42])=[CH:38][CH:39]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH2:28][NH:29][CH:30]([CH3:32])[CH3:31])[C:9]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[C:18]4[C@H:25]([CH3:26])[CH2:24][C@@H:23]([OH:27])[C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:15][CH2:16]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 24788740Ipatasertib

Product 1

HCID 117993311Ipatasertib tosylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

(S)-2-(4-Chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one free base, 202.4 mg, was dissolved in acetonitrile, 10 mL. p-Toluenesulfonic acid monohydrate, 83.5 mg, was dissolved in acetonitrile, 10 mg, and the two solutions mixed. The solution was slowly evaporated under a stream of nitrogen. The crystaline tosylate salt was analyzed after evaporating over 3 weeks (See FIG. 3).

Workup

  1. addition10 mg, and the two solutions mixed
  2. customThe solution was slowly evaporated under a stream of nitrogen
  3. customafter evaporating over 3 weeks (See FIG. 3)

Sources & evidence

ORD record
ord-78f1e24269a043fb86b862ea8bc3d1fb
Source dataset
uspto-grants-2016_04
Patent number
US09315471B2

Reaction notes

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