Methanesulfonic Acid → HCID 86645853, compound

HRID 1256468Notes

Reaction equation

HRID 1256468 reaction equation
[F:1][CH:2]([F:47])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][N:28]([S:31]([CH3:34])(=[O:33])=[O:32])[CH2:27][CH2:26]4)(=[O:22])=[O:21])[CH2:16][CH2:15]3)[N:11]=[C:10]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[N:9]=2)[C:6]2[CH:41]=[CH:42][CH:43]=[C:44]([O:45][CH3:46])[C:5]=2[N:4]=1.[CH3:48][S:49]([OH:52])(=[O:51])=[O:50]>CO>[CH3:48][S:49]([OH:52])(=[O:51])=[O:50].[F:47][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][N:17]([S:20]([CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][N:28]([S:31]([CH3:34])(=[O:32])=[O:33])[CH2:29][CH2:30]4)(=[O:21])=[O:22])[CH2:18][CH2:19]3)[N:11]=[C:10]([N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)[N:9]=2)[C:6]2[CH:41]=[CH:42][CH:43]=[C:44]([O:45][CH3:46])[C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 46917647HCID 46917647, compound

Product 1

HCID 86645853HCID 86645853, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-(difluoromethyl)-4-methoxy-1-[4-[4-({2-[4-(methylsulfonyl)-1-piperazinyl]ethyl}sulfonyl)-1-piperazinyl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole from the previous step in MeOH (50 mL) was treated with methanesulfonic acid (33 mg, 1.1 equiv.) to give a clear solution. The solvent was removed under vacuum and the residue was washed with EtOAc to give 2-(difluoromethyl)-4-methoxy-1-[4-[4-({2-[4-(methylsulfonyl)-1-piperazinyl]ethyl}sulfonyl)-1-piperazinyl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1H-benzimidazole methanesulfonate: mp (MeOH/EtOAc) 232-235° C.; Anal. Calcd. for C28H42F2N10O9S3.0.5H2O: C, 41.7; H, 5.4; N, 17.4. Found: C, 41.7; H, 5.3; N, 17.2%.

Workup

  1. customto give a clear solution
  2. customThe solvent was removed under vacuum
  3. washthe residue was washed with EtOAc

Sources & evidence

ORD record
ord-07ffba350dd946b4b35b5ac0dbe5fd41
Source dataset
uspto-grants-2013_06
Patent number
US08461158B2

Reaction notes

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