Chloride → (3-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-propyl)-trimethyl-ammonium benzenesulfonate

HRID 2203395Notes

Reaction equation

HRID 2203395 reaction equation
[Cl-].[S:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:5])(=[O:4])=[O:3].C1(S(O)(=O)=O)C=CC=CC=1.[Br-].[C:23]([C:25]1[CH:26]=[CH:27][C:28]([C@H:38]2[N:43]3[C:44](=[O:47])[NH:45][N:46]=[C:42]3[N:41]([C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([C:54]([F:57])([F:56])[F:55])[CH:49]=3)[C:40]([CH3:58])=[C:39]2[C:59]([O:61][CH3:62])=[O:60])=[C:29]([CH2:31][CH2:32][CH2:33][N+:34]([CH3:37])([CH3:36])[CH3:35])[CH:30]=1)#[N:24]>CC#N.O>[C:6]1([S:2]([O-:5])(=[O:4])=[O:3])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:23]([C:25]1[CH:26]=[CH:27][C:28]([C@H:38]2[N:43]3[C:44](=[O:47])[NH:45][N:46]=[C:42]3[N:41]([C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([C:54]([F:57])([F:56])[F:55])[CH:49]=3)[C:40]([CH3:58])=[C:39]2[C:59]([O:61][CH3:62])=[O:60])=[C:29]([CH2:31][CH2:32][CH2:33][N+:34]([CH3:37])([CH3:36])[CH3:35])[CH:30]=1)#[N:24]

Participants

6

Reactant 4

HCID 312ChlorideHCID 7371Benzenesulfonic AcidHCID 91526Benzenesulfonate2×HCID 76285275(3-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-propyl)-trimethyl-ammonium bromide

Product 1

HCID 76285277(3-{5-Cyano-2-[(R)-6-methoxycarbonyl-7-methyl-3-oxo-8-(3-trifluoromethyl-phenyl)-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidin-5-yl]-phenyl}-propyl)-trimethyl-ammonium benzenesulfonate

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Amberlite IRA 458 ‘chloride’ resin (40 g, wet) was converted to the besylate equivalent by passing a solution of benzene sulphonic acid (400 mL, 10% aqueous solution) through the resin in a glass column at a slow rate of 5-10 mL/minute. Following this, the resin was washed with water until the filtrate had a pH of ˜5/6. The resin was stored “damp” prior to use. A solution of Example 40 (1 g, 1.57 mmol) in a round-bottom flask (250 mL) was treated with 30% MeCN/water (60 mL) and then mixed with the besylate resin (40 g, wet). The resulting mixture was gently agitated by slowly rotating the flask on a Buchi evaporator for 50 minutes at atmospheric pressure. The contents were placed in a resin tube, then filtered and washed with 30% MeCN/water and the filtrate was freeze dried to give the title compound as a white electrostatic solid (1.01 g).

Workup

  1. washwas washed with water until the filtrate
  2. customon a Buchi evaporator for 50 minutes at atmospheric pressure
  3. customThe contents were placed in a resin tube
  4. filtrationfiltered
  5. washwashed with 30% MeCN/water
  6. customdried

Sources & evidence

ORD record
ord-9afd9b6964164cecb2921f4373441bc6
Source dataset
uspto-grants-2016_06
Patent number
US09365577B2

Reaction notes

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