N-(4-fluorophenyl)-N'-(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide → N-(4-fluorophenyl)-N'-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]cyclopropane-1,1-dicarboxamide

HRID 1011296Notes

Reaction equation

HRID 1011296 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:29]=[CH:28][N:27]=[C:26]5[N:30](C6CCCCO6)[N:31]=[CH:32][C:25]=45)=[CH:19][CH:18]=3)=[O:15])[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.Cl.O1CCOCC1>CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2([C:14]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][C:24]4[N:29]=[CH:28][N:27]=[C:26]5[NH:30][N:31]=[CH:32][C:25]=45)=[CH:21][CH:22]=3)=[O:15])[CH2:13][CH2:12]2)=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11699227N-(4-fluorophenyl)-N'-(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamideHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 11590092N-(4-fluorophenyl)-N'-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]cyclopropane-1,1-dicarboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added N-(4-fluorophenyl)-N′-(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl)cyclopropane-1,1-dicarboxamide (0.050 mg, 0.10 mmol, 1.0 eq.) and 4M HCl/Dioxane (5 ml). After 5 minutes ether was added. The resulting solid was filtered and washed twice with ether. The solid was further dried under vacuum to give N-(4-fluorophenyl)-N′-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]cyclopropane-1,1-dicarboxamide (0.027 g, 67% yield). 1H NMR (400 MHz, DMSO): 10.20 (s, 1H), 10.10 (s, 1H), 8.50 (s, 1H), 8.06 (s, 1H), 7.75 (m, 2H), 7.67 (m, 2H), 7.27 (m, 2H), 7.13 (m, 2H), 4.47 (bs, 1H), 1.47 (s, 4H); MS (ESI) for C22H17FN6O3: 433 (MH+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. filtrationThe resulting solid was filtered
  3. washwashed twice with ether
  4. customThe solid was further dried under vacuum

Sources & evidence

ORD record
ord-aeb3522610bc4d6eb8c9c3cd0db48b6b
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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