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Triethylamine → n-[4-(5-(1h-1,2,4-Triazol-5-yl)(1h-indazol-3-yl))phenyl]-2-furyl carboxamide

HRID 1353797
Notes
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Reaction equation

HRID 1353797 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9]([C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)=[N:8]1.C(N(CC)CC)C.[O:54]1[CH:58]=[CH:57][CH:56]=[C:55]1Cl.[C:60](=O)(O)[O-:61].[Na+]>O1CCCC1>[NH:17]1[C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3[C:40]2[CH:45]=[CH:44][C:43]([NH:46][C:60]([C:55]3[O:54][CH:58]=[CH:57][CH:56]=3)=[O:61])=[CH:42][CH:41]=2)=[N:20][CH:19]=[N:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1378562-ChlorofuranHCID 516892Sodium BicarbonateHCID 224801494-{1-Perhydro-2h-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]1h-indazol-3-yl}phenylamine

Product 1

HCID 11291651n-[4-(5-(1h-1,2,4-Triazol-5-yl)(1h-indazol-3-yl))phenyl]-2-furyl carboxamideYield 5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]1H-indazol-3-yl}phenylamine (0.300 g, 0.498 mmol) was added tetrahydrofuran (4.50 mL), triethylamine (0.345 mL, 2.48 mmol), and 2-furyl chloride (0.058 mL, 0.735 mmol). The mixture was stirred for 16 h at ambient temperature and poured into saturated sodium bicarbonate (50 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and evaporated. Purification by preparative HPLC (30–80% acetonitrile/water) followed by washing with saturated sodium bicarbonate and extraction with ethyl acetate gave the title compound (0.0086 g, 5% yield). 1H NMR (DMSO-d6) δ 8.75 (d, 1H), 8.10 (m, 6H), 7.74 (m, 1H), 7.39 (d, 1H), 6.75 (m, 1H). ES-MS (m/z) 371 [M+1]+

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by preparative HPLC (30–80% acetonitrile/water)
  7. washby washing with saturated sodium bicarbonate and extraction with ethyl acetate

Sources & evidence

ORD record
ord-fa8d2f727b1a47d28ee2e3a508557352
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07220771B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes