Diisopropylethylamine → HCID 89473633, compound

HRID 521244Notes

Reaction equation

HRID 521244 reaction equation
FC(F)(F)C([O-])=O.[C:8]([C:11]1[C:12]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:13][N:14]([C:16]2([CH2:20][C:21]#[N:22])[CH2:19][NH2+:18][CH2:17]2)[CH:15]=1)(=[O:10])[NH2:9].CCN(C(C)C)C(C)C.[F:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([N:46]=[C:47]=[O:48])[CH:41]=1>CC#N.CS(C)=O>[C:21]([CH2:20][C:16]1([N:14]2[CH:15]=[C:11]([C:8]([NH2:9])=[O:10])[C:12]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:13]2)[CH2:17][N:18]([C:47](=[O:48])[NH:46][C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([F:39])[CH:41]=2)[CH2:19]1)#[N:22]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230643-Fluorophenyl isocyanateHCID 86729391HCID 86729391, compound

Product 1

HCID 89473633HCID 89473633, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Procedure

3-[4-Carbamoyl-3-(phenylamino)-1H-pyrazol-1-yl]-3-(cyanomethyl)azetidinium trifluoroacetate (Intermediate #38-2) (25 mg, 0.060 mmol) was dissolved in MeCN (0.50 mL) and treated with DIPEA (0.020 mL, 0.12 mmol) and 1-fluoro-3-isocyanatobenzene (0.010 mL, 0.090 mmol). The reaction mixture was stirred at ambient temperature for 2 hours and then diluted with DMSO (1.0 mL) and purified directly by reverse-phase preparative HPLC (using a gradient elution of 5-95% MeCN/water, with 0.1% v/v NH4OH modifier). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound, Example #38-1.

Workup

  1. custompurified directly by reverse-phase preparative HPLC (
  2. washa gradient elution of 5-95% MeCN/water
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-392dcade48544d3aa08df68f1618e56c
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

Loading…