Hydrochloric Acid → HCID 178522143, compound

HRID 1011307Notes

Reaction equation

HRID 1011307 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[N:32]=[CH:31][N:30]=[C:29]5[C:25]=4[N:26]=[CH:27][N:28]5C4CCCCO4)=[CH:19][CH:18]=3)=[O:15])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[N:32]=[CH:31][N:30]=[C:29]5[C:25]=4[N:26]=[CH:27][NH:28]5)=[CH:19][CH:18]=3)=[O:15])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11699228HCID 11699228, compound

Product 1

HCID 178522143HCID 178522143, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-(4-fluorophenyl)-N′-(4-{[9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl]oxy}phenyl)-cyclopropane-1,1-dicarboxamide (430 mg, 0.83 mmol) in 30 mL of dioxane was added 3 mL of 4N HCl in dioxane. The reaction mixture was stirred at room temperature for 1 h. After removal of solvent in vacuo, the reaction mixture triturated with ether, affording N-(4-fluorophenyl)-N′-[4-(9H-purin-6-yloxy)phenyl]cyclopropane-1,1-dicarboxamide (300 mg, 83% yield) as a colorless solid. 1H NMR (400 MHz, DMSO, d6): δ 10.20 (s, 1H), 10.10 (s, 1H), 8.6 (s, 1H), 8.4 (s, 1H), 7.6-7.8 (m, 4H), 7.1-7.3 (m, 4H), 1.45 (s, 4H). MS (ESI) for C22H17FN6O3: 433 (MH+).

Workup

  1. customAfter removal of solvent in vacuo
  2. customthe reaction mixture triturated with ether

Sources & evidence

ORD record
ord-55177fc2b8404292806755803eb2be34
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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