Dimethylformamide → HCID 86660772, compound

HRID 1046869Notes

Reaction equation

HRID 1046869 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].C1O[CH2:23][CH2:22]OCCOCCOCCOCCOC1.CI.C(OC(=O)N[C:37]1[N:66]=[C:40]2[N:41]([C:56]3[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([F:65])([F:64])[F:63])[CH:57]=3)[C:42]([CH3:55])=[C:43]([C:53]#[N:54])[C@@H:44]([C:45]3[CH:50]=[CH:49][C:48]([C:51]#[N:52])=[CH:47][CH:46]=3)[N:39]2[N:38]=1)C1C=CC=CC=1.C[N:69]([CH:71]=[O:72])[CH3:70]>>[CH2:1]([O:4][C:71](=[O:72])[NH:69][CH2:70][C:37]1[N:66]=[C:40]2[N:41]([C:56]3[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([F:65])([F:63])[F:64])[CH:57]=3)[C:42]([CH3:55])=[C:43]([C:53]#[N:54])[C@@H:44]([C:45]3[CH:46]=[CH:47][C:48]([C:51]#[N:52])=[CH:49][CH:50]=3)[N:39]2[N:38]=1)[C:23]1[CH:22]=[CH:44][CH:43]=[CH:42][CH:55]=1

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-6e8d3e9688b146bdb63238e1c4b96547
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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