Potassium Phosphate, Tribasic → HCID 66684666, compound

HRID 579198Notes

Reaction equation

HRID 579198 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][C:15](=[O:17])[N:14]([C:18]3[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[S:20][C:19]=3[C:29]([OH:31])=[O:30])[C@H:13]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N:46]1[CH:51]=[C:50](B(O)O)[CH:49]=[N:48][CH:47]=1>C(#N)C>[CH:32]1([C@@H:13]2[CH2:12][N:11]([S:8]([C:5]3[CH:6]=[N:7][C:2]([C:50]4[CH:51]=[N:46][CH:47]=[N:48][CH:49]=4)=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:16][C:15](=[O:17])[N:14]2[C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[S:20][C:19]=2[C:29]([OH:31])=[O:30])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86684770HCID 86684770, compound

Product 1

HCID 66684666HCID 66684666, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 3-[(R)-4-(6-chloro-pyridine-3-sulfonyl)-2-cyclohexyl-6-oxo-piperazin-1-yl]-5-phenyl-thiophene-2-carboxylic acid (1.20 g, 2.14 mmol, 1.0 equiv) in acetonitrile (15.0 mL) was added potassium phosphate (8.58 ml, 1.0 M aqueous solution, 4.0 equiv) and chloro(2-dicyclohexyl phosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)[2-(2-amino ethyl)phenyl] Pd(II) Me-t-butyl ether adduct (0.32 g, 0.43 mmol, 0.2 equiv) at room temperature. The mixture was stirred at room temperature for 10 minutes to form a stock solution. To 0.8 mL of above solution was added 5-pyrimidinyl boronic acid (17.7 mg, 0.143 mmol, 2.0 equiv) and acetonitrile (0.5 mL) at room temperature. The mixture was stirred at 80° C. for 4 hours. The mixture was purified by HPLC (0.1% NH4OH) to afford the product (15.9 mg, 36.9%). MS: 603.2 [M−H+].

Workup

  1. customto form a stock solution
  2. stirringThe mixture was stirred at 80° C. for 4 hours
  3. customThe mixture was purified by HPLC (0.1% NH4OH)

Sources & evidence

ORD record
ord-6a9d5b90c20c49ad93c57c34343248ed
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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