1,1'-Carbonyldiimidazole → HCID 136931788, compound

HRID 2207408Notes

Reaction equation

HRID 2207408 reaction equation
C1CCN2C(=NCCC2)CC1.[OH:12][C:13](C(F)(F)F)=O.OC(C(F)(F)F)=O.[OH:26]/[N:27]=[C:28](\[NH2:57])/[C:29]([CH3:56])([NH:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[C:42]([NH:44][C:45]3[N:50]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:48]=[CH:47][N:46]=3)[CH:41]=[C:40]([CH3:55])[CH:39]=2)=[CH:34][N:33]=1)[CH3:30].C1N=CN(C(N2C=NC=C2)=O)C=1>O1CCOCC1>[CH3:55][C:40]1[CH:39]=[C:38]([C:35]2[CH:36]=[CH:37][C:32]([NH:31][C:29]([C:28]3[NH:57][C:13](=[O:12])[O:26][N:27]=3)([CH3:30])[CH3:56])=[N:33][CH:34]=2)[CH:43]=[C:42]([NH:44][C:45]2[N:50]=[C:49]([C:51]([F:54])([F:53])[F:52])[CH:48]=[CH:47][N:46]=2)[CH:41]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178428302HCID 178428302, compound

Product 1

HCID 136931788HCID 136931788, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

DBU (10.0 μL, 0.066 mmol) was added to a mixture of (1Z)—N′-hydroxy-2-methyl-2-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]amino}propanimidamide bis-TFA salt (14.0 mg, 0.025 mmol) and CDI (4.26 mg, 0.026 mmol) in dioxane (100 μL). The reaction was stirred at room temperature overnight. The reaction mixture was filtered, diluted with DMF (500 μL), and directly purified by reverse phase HPLC. The isolated material was repurified by silica gel chromatography (0-100% ethyl acetate in hexanes with 1% triethylamine and then 20% methanol in dichloromethane) to yield 3-(2-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]amino}propan-2-yl)-1,2,4-oxadiazol-5(4H)-one. MS APCI calc'd for C22H21F3N7O2 [M+H]+ 472. found 472. 1H NMR (500 MHz, CDCl3) δ 8.67 (d, J=5.2 Hz, 1H), 8.34 (s, 1H), 7.79 (d, J=11.5 Hz, 2H), 7.41 (s, 1H), 7.31 (s, 1H), 7.05 (d, J=5.2 Hz, 2H), 6.64 (d, J=9.1 Hz, 1H), 2.43 (s, 3H), 1.80 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additiondiluted with DMF (500 μL)
  3. customdirectly purified by reverse phase HPLC
  4. customThe isolated material was repurified by silica gel chromatography (0-100% ethyl acetate in hexanes with 1% triethylamine

Sources & evidence

ORD record
ord-e3c40de96c794e55afa6d939aa640a73
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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