Water → HCID 178522013, compound

HRID 1349908Notes

Reaction equation

HRID 1349908 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.[Cl:47][C:48]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:49]=1[CH2:50]Cl.[OH2:57]>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:50]([C:49]3[CH:52]=[CH:53][C:54]([Cl:56])=[CH:55][C:48]=3[Cl:47])=[O:57])[CH:43]=[CH:44][CH:45]=2)=[N:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 72122,4-Dichlorobenzyl 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 178522013HCID 178522013, compoundYield 55%

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 (0.200 g, 0.33 mmol) in pyridine (2 mL) was added 2,4-dichlorobenzyl chloride (0.056 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 (0.070 g, 55% yield) which was isolated by filtration: 1H NMR (DMSO-d6) δ 14.20 (br s, 1H), 13.44 (s, 1H), 10.75 (s, 1H), 8.69 (s, 1H), 8.36 (s, 1H), 8.06 (d, 1H), 7.78 (m, 3H), 7.68 (d, 2H), 7.55 (m, 2H); ES-MS (m/z) 449 [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-a59001e8c6734d31810f12432040c919
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

Loading…