Dimethylformamide → HCID 86660772, compound

HRID 2200969Notes

Reaction equation

HRID 2200969 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].C1O[CH2:23][CH2:22]OCCOCCOCCOCCOC1.CI.[C:27]([C:29]1[C@@H:34]([C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)[N:33]2[N:43]=[C:44](NC(=O)OCC3C=CC=CC=3)[N:45]=[C:32]2[N:31]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([C:63]([F:66])([F:65])[F:64])[CH:58]=2)[C:30]=1[CH3:67])#[N:28].C[N:69]([CH:71]=[O:72])[CH3:70]>>[C:27]([C:29]1[C@@H:34]([C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)[N:33]2[N:43]=[C:44]([CH2:70][NH:69][C:71](=[O:72])[O:4][CH2:1][C:23]3[CH:22]=[CH:67][CH:30]=[CH:29][CH:27]=3)[N:45]=[C:32]2[N:31]([C:57]2[CH:62]=[CH:61][CH:60]=[C:59]([C:63]([F:64])([F:65])[F:66])[CH:58]=2)[C:30]=1[CH3:67])#[N:28]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 70223867HCID 70223867, compound

Product 1

HCID 86660772HCID 86660772, compound

Procedure

Potassium carbonate (6.0 mg, 43 μmol, 1.6 eq.), 18-crown-6 (11.4 mg, 43 μmol, 1.5 eq.) and methyl iodide (6.1 mg, 53 μmol, 2.0 eq.) were added to a solution of benzyl {(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}carbamate (15 mg, 27 μmol) in DMF (2 ml). The reaction mixture was stirred at RT for 12 h and then concentrated under reduced pressure and purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (13.3 mg, 86% of theory).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  3. customAfter lyophilization, the product was obtained as a solid (13.3 mg, 86% of theory)

Sources & evidence

ORD record
ord-84857624847845288cbf6417455e9f84
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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