Triethylamine → HCID 22147131, compound

HRID 1824446Notes

Reaction equation

HRID 1824446 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.[C:25]([C:29]1[CH:30]=[C:31](C(O)=O)[N:32]([C:34]2[CH:35]=[N:36][C:37]([CH3:40])=[N:38][CH:39]=2)[N:33]=1)([CH3:28])([CH3:27])[CH3:26].C(C1C=C([NH:54][C:55]([NH:57][C:58]2[C:67]3[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=3)[C:61]([O:68][C:69]3[CH:74]=[CH:73][N:72]=[C:71]([NH:75][CH2:76][CH:77]4[CH2:79][CH2:78]4)[N:70]=3)=[CH:60][CH:59]=2)=[O:56])N(C)N=1)(C)(C)C>C(COC)OC.C1COCC1>[C:25]([C:29]1[CH:30]=[C:31]([NH:54][C:55]([NH:57][C:58]2[C:67]3[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=3)[C:61]([O:68][C:69]3[CH:74]=[CH:73][N:72]=[C:71]([NH:75][CH2:76][CH:77]4[CH2:79][CH2:78]4)[N:70]=3)=[CH:60][CH:59]=2)=[O:56])[N:32]([C:34]2[CH:39]=[N:38][C:37]([CH3:40])=[N:36][CH:35]=2)[N:33]=1)([CH3:26])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22147130HCID 22147130, compoundHCID 22147192HCID 22147192, compound

Product 1

HCID 22147131HCID 22147131, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Diphenylphosphoryl azide (DPPA) (0.09 mL, 0.423 mmol, 1.1 equiv.) and triethylamine (0.075 mL, 0.54 mmol, 1.4 equiv.) were added to 5-tert-butyl-2-(2-methylpyrimidin-5-yl)-2H-pyrazole-3-carboxylic acid (100 mg, 0.384 mmol, 1.0 equiv.) in 2.0 mL anhydrous dimethoxyethane in a sealed tube. The mixture was heated at 85° C. for 2.5 h, then a solution of the cyclopropylmethylaminopyrimidine-ether intermediate (see Example 4)(118 mg, 0.38 mmol, 1.0 equiv.) in 3.0 mL anhydrous THF was added and the resulting mixture stirred at room temperature overnight. The solvent was removed in vacuo and the crude urea was purified by column chromatography on silica gel using 0–65% EtOAc in hexanes eluent mixtures. The product was purified further by prep-HPLC affording 15 mg of the title compound (7% yield).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude urea was purified by column chromatography on silica gel using 0–65% EtOAc in hexanes eluent mixtures
  3. customThe product was purified further

Sources & evidence

ORD record
ord-a2b66615ab3e40e0aac226bbf03d4dd8
Source dataset
uspto-grants-2006_05
Patent number
US07041669B2

Reaction notes

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