Ethanol → HCID 46834071, compound

HRID 1516443Notes

Reaction equation

HRID 1516443 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH2:15][CH2:14][CH:13]([NH:16][C:17]3[N:22]=[C:21]([N:23]4[C:27]5[CH:28]=[CH:29][CH:30]=[C:31](I)[C:26]=5[N:25]=[N:24]4)[CH:20]=[CH:19][N:18]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:4][CH2:3]1.[C:33]([O-:36])([O-])=O.[Na+].[Na+].[C:39]1(C)[CH:44]=CC=C[CH:40]=1.CCO>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:36]1[CH:33]=[CH:44][C:39]([C:31]2[C:26]3[N:25]=[N:24][N:23]([C:21]4[CH:20]=[CH:19][N:18]=[C:17]([NH:16][CH:13]5[CH2:14][CH2:15][CH:10]([C:8]([N:5]6[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]6)=[O:9])[CH2:11][CH2:12]5)[N:22]=4)[C:27]=3[CH:28]=[CH:29][CH:30]=2)=[CH:40]1

Participants

7

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 67425529HCID 67425529, compound

Product 1

HCID 46834071HCID 46834071, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of (4-hydroxy-piperidin-1-yl)-{4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-yl-amino]-cyclohexyl}-methanone (274 mg) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)-furan (102 mg) was placed in a screw cap pressure flask, and Na2CO3 (2 M aq, 0.7 mL, degassed), toluene (5 mL, degassed) and EtOH (5 mL) added. To this was added Pd(PPh3)4 (20 mg), the flask sealed, and the mixture stirred overnight at 110° C. The reaction mixture was then cooled to RT, diluted in water, extracted in DCM, washed with water and brine, dried over Na2SO4, and the solvent stripped to yield a crude solid. The crude product was chromatographed on silica, and eluted with 0-60% Magic Base/DCM, titurated in Et2O overnight, filtered, and evaporated to yield {4-[4-(4-furan-3-yl-benzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-(4-hydroxy-piperidin-1-yl)-methanone (Compound 9, 103 mg). mp=243.0-244.0° C.; M+H=488.

Workup

  1. customcap pressure flask
  2. customthe flask sealed
  3. temperatureThe reaction mixture was then cooled to RT
  4. extractionextracted in DCM
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. customto yield a crude solid
  8. customThe crude product was chromatographed on silica
  9. washeluted with 0-60% Magic Base/DCM
  10. waittiturated in Et2O overnight
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-e3fe54f138c74362ae7b7b1f03ed036c
Source dataset
uspto-grants-2012_07
Patent number
US08227478B2

Reaction notes

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