Sodium Hydroxide → HCID 178510574, compound

HRID 1441297Notes

Reaction equation

HRID 1441297 reaction equation
O1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][N:15]=[C:14]([C:24]#[N:25])[N:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+].FC(F)(F)C([O-])=O.[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]1[NH:42][C:43]([CH:46]2[CH2:51][CH2:50][NH2+:49][CH2:48][CH2:47]2)=[N:44][N:45]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.Cl.C(OCC)(=O)C.ClCCl.CCN(C(C)C)C(C)C>[C:18]1([C:17]2[C:12]([C:9]3[CH:8]=[CH:7][C:6]([CH2:2][N:49]4[CH2:50][CH2:51][CH:46]([C:43]5[NH:42][C:41]([C:36]6[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=6)=[N:45][N:44]=5)[CH2:47][CH2:48]4)=[CH:11][CH:10]=3)=[N:13][C:14]([C:24]#[N:25])=[N:15][CH:16]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

10

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 5049666Sodium triacetoxyborohydrideHCID 67343830HCID 67343830, compoundHCID 178525659HCID 178525659, compound

Product 1

HCID 178510574HCID 178510574, compound

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of 4-[4-(1,3-dioxolan-2-yl)phenyl]-5-phenylpyrimidine-2-carbonitrile (165 mg, 0.501 mmol) in THF (7 mL) and 6N HCl (4 mL) was stirred at rt for 1 h. The reaction mixture was neutralized with sodium hydroxide and diluted with ethyl acetate (50 mL). The solution was washed with water (2×25 mL) and dried over magnesium sulfate. Hunig's base (1 mL) was added to the solution and it was then added to a solution of 4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidinium trifluoroacetate (206 mg, 0.600 mmol) in dichloromethane (5 mL) and Hunig's base (1 mL). The reaction mixture was concentrated under reduced pressure and diluted with dichloromethane (10 mL). Sodium triacetoxyborohydride (320 mg, 1.509 mmol) was added and stirred over night. The reaction mixture was basified with sodium hydroxide, extracted with ethyl acetate (50 mL)j and purified on reverse phase HPLC to yield 5-phenyl-4-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)pyrimidine-2-carbonitrile as a solid. MS (EI) m/z 499 (M+1).

Workup

  1. washThe solution was washed with water (2×25 mL)
  2. dry with materialdried over magnesium sulfate
  3. additionHunig's base (1 mL) was added to the solution and it
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additiondiluted with dichloromethane (10 mL)
  6. extractionextracted with ethyl acetate (50 mL)j
  7. custompurified on reverse phase HPLC

Sources & evidence

ORD record
ord-b3feb0418a444d8bbdb691819902ee2d
Source dataset
uspto-grants-2010_02
Patent number
US07655649B2

Reaction notes

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