Sodium Carbonate → HCID 46833492, compound

HRID 1516436Notes

Reaction equation

HRID 1516436 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]1([CH3:42])[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O.[C:43]([O-])([O-])=[O:44].[Na+].[Na+]>>[NH4+:5].[OH-:1].[CH3:43][OH:44].[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]([C:34]6[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=6[CH3:42])[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

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 67425529HCID 67425529, compound

Product 2

HCID 21894508Ammonium hydroxide methanolYield 1%HCID 46833492HCID 46833492, compoundYield 73%

Procedure

A mixture of (4-hydroxy-piperidin-1-yl)-{4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-yl-amino]-cyclohexyl}-methanone (0.4 g), o-tolylboronic acid (0.104 g) and Na2CO3 (2 M, 1.1 mL, degassed) was degassed with argon for 5 min, then stirred at RT under N2 for 15 min. To this was added Pd(PPh3)4 (0.025 g) with toluene (13 mL, degassed) and EtOH (1 mL), and the mixture stirred overnight at 110° C. The reaction mixture was then diluted in water, extracted in DCM, washed with water and brine, dried over Na2SO4, and the solvent stripped to yield a solid. The solid was flash-chromatographed on silica, eluting with DCM: 1% NH4OH-MeOH (1000:50) to provide (4-hydroxy-piperidin-1-yl)-{4-[4-(4-o-tolyl-benzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-methanone (Compound 2, 0.272 g, 73%) as an off-white solid. Mp=224-226° C.; M+H=512.

Workup

  1. customwas degassed with argon for 5 min
  2. additionTo this was added Pd(PPh3)4 (0.025 g) with toluene (13 mL, degassed) and EtOH (1 mL)
  3. stirringthe mixture stirred overnight at 110° C
  4. additionThe reaction mixture was then diluted in water
  5. extractionextracted in DCM
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. customto yield a solid
  9. customThe solid was flash-chromatographed on silica
  10. washeluting with DCM

Sources & evidence

ORD record
ord-5218bdedd69e4cef84d0f1a00eb4f136
Source dataset
uspto-grants-2012_07
Patent number
US08227478B2

Reaction notes

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