Methanesulfonic Acid → Pictilisib Bismesylate

HRID 2188624Notes

Reaction equation

HRID 2188624 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[C:13]4[S:18][C:17]([CH2:19][N:20]5[CH2:25][CH2:24][N:23]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:22][CH2:21]5)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:36][S:37]([OH:40])(=[O:39])=[O:38]>ClCCl.CO>[S:37]([OH:40])(=[O:39])(=[O:38])[CH3:36].[S:37]([OH:40])(=[O:39])(=[O:38])[CH3:36].[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)[C:13]4[S:18][C:17]([CH2:19][N:20]5[CH2:25][CH2:24][N:23]([S:26]([CH3:29])(=[O:27])=[O:28])[CH2:22][CH2:21]5)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 17755052Pictilisib

Product 1

HCID 56972143Pictilisib Bismesylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To 2-(1H-indazol-4-yl)-6-(4-methanesulfonyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (2.00 g, 3.89 mmol) in dichloromethane (50 ml) and methanol (20 ml) was added methanesulfonic acid (2 equiv., 505 ul). The reaction mixture was stirred for 3 hours at room temperature during which time a white precipitate gradually crashed out. Volatiles were removed in vacuo, the residue was triturated with diethyl ether, the solvent decanted and the solid dried under vacuum to give the title compound (2.70 g).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue was triturated with diethyl ether
  3. customthe solvent decanted
  4. customthe solid dried under vacuum

Sources & evidence

ORD record
ord-d54d2ac2295b4e8898a0c7f49ed755f4
Source dataset
uspto-grants-2012_12
Patent number
US08324206B2

Reaction notes

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