Hydrochloric Acid → N-[2-({4-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1-piperazinyl}sulfonyl)ethyl]-N,N-dimethylamine hydrochloride

HRID 516307Notes

Reaction equation

HRID 516307 reaction equation
[F:1][CH:2]([F:40])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([N:20]3[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])(=[O:28])=[O:27])[CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:5]=2[N:4]=1.[ClH:41]>CO>[ClH:41].[F:40][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([N:20]3[CH2:21][CH2:22][N:23]([S:26]([CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])(=[O:28])=[O:27])[CH2:24][CH2:25]3)[N:9]=2)[C:6]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:5]=2[N:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 46917573HCID 46917573, compound

Product 1

HCID 67544336N-[2-({4-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1-piperazinyl}sulfonyl)ethyl]-N,N-dimethylamine hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of N-[2-({4-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1-piperazinyl}sulfonyl)ethyl]-N,N-dimethylamine from the previous step in MeOH (100 mL) was added a slight excess of 1.25 M HCl in MeOH (0.45 mL). The resulting clear solution was concentrated to dryness. The residue was recrystallized from MeOH/EtOAc to give 0.51 g (83% yield for the last two steps) of N-[2-({4-[4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-1-piperazinyl}sulfonyl)ethyl]-N,N-dimethylamine hydrochloride: mp (MeOH/EtOAc) 222-224° C.; Anal. Calcd. for C24H34ClF2N9O4S: C, 46.6; H, 5.5; N, 20.4; Cl, 5.7. Found: C, 46.3; H, 5.7; N, 20.0; Cl, 5.7%.

Workup

  1. concentrationThe resulting clear solution was concentrated to dryness
  2. customThe residue was recrystallized from MeOH/EtOAc

Sources & evidence

ORD record
ord-fd6fa0b04f0e4eb5a6502191d3e2c556
Source dataset
uspto-grants-2015_08
Patent number
US09108980B2

Reaction notes

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