Water → HCID 178454458, compound

HRID 1353965Notes

Reaction equation

HRID 1353965 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:41]=[C:42]([NH2:46])[CH:43]=[CH:44][CH:45]=2)=[N:8]1.[CH3:47][CH:48]([CH3:52])[C:49](Cl)=[O:50].O>N1C=CC=CC=1>[NH:18]1[CH:19]=[N:20][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:41]=[C:42]([NH:46][C:49](=[O:50])[CH:48]([CH3:52])[CH3:47])[CH:43]=[CH:44][CH:45]=2)=[N:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 62325Isobutyryl chlorideHCID 211011823-(1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine

Product 1

HCID 178454458HCID 178454458, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine (0.190 g, 0.33 mmol) in pyridine (2 mL) was added 2-methylpropanoyl chloride (0.042 mL, 0.40 mmol). The reaction was stirred at room temperature for 15 h. Water (10 mL) was added and the solid collected by suction filtration. The solid was dried in a vacuum oven for 3 h. The residue was dissolved in 4 N hydrochloric acid in 1,4-dioxane (10 mL) and the mixture was stirred at room temperature for 2 h. After neutralization with aqueous sodium bicarbonate, the reaction mixture was extracted with ethyl acetate. The combined organic fractions were dried over anhydrous sodium sulfate, filtered and evaporated. Addition of dichloromethane (10 mL) to the residue gave the title compound (0.005 g, 5% yield) which was isolated by filtration: 1H NMR (DMSO-d6) δ 10.02 (s, 1H), 8.65 (s, 1H), 8.21 (s, 1H), 8.10 (br s, 1H), 7.78 (d, 1H), 7.65 (m, 2H), 7.45 (t, 1H), 2.63 (m, 1H), 1.19 (d, 6H); ES-MS (m/z) 347 [M+1]+.

Workup

  1. filtrationthe solid collected by suction filtration
  2. customThe solid was dried in a vacuum oven for 3 h
  3. dissolutionThe residue was dissolved in 4 N hydrochloric acid in 1,4-dioxane (10 mL)
  4. stirringthe mixture was stirred at room temperature for 2 h
  5. extractionAfter neutralization with aqueous sodium bicarbonate, the reaction mixture was extracted with ethyl acetate
  6. dry with materialThe combined organic fractions were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. additionAddition of dichloromethane (10 mL) to the residue

Sources & evidence

ORD record
ord-dcf23918e0d24c3eb5ca67ea132939f8
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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