Potassium Carbonate → HCID 57496310, compound

HRID 719483Notes

Reaction equation

HRID 719483 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]3[N:20]([C:23]4[CH:28]=[CH:27][C:26](I)=[CH:25][C:24]=4[CH3:30])[N:21]=[CH:22][C:15]=23)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:31][S:32]([CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)(=[O:34])=[O:33].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[CH:18][N:17]=[C:16]3[N:20]([C:23]4[CH:28]=[CH:27][C:26]([N:40]5[CH2:39][CH2:38][N:37]([CH2:36][CH2:35][S:32]([CH3:31])(=[O:33])=[O:34])[CH2:42][CH2:41]5)=[CH:25][C:24]=4[CH3:30])[N:21]=[CH:22][C:15]=23)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 38019591-(2-(Methylsulfonyl)ethyl)piperazineHCID 57496369HCID 57496369, compound

Product 1

HCID 57496310HCID 57496310, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-[1-(4-iodo-2-methyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (78 mg, 0.15 mmol), 1-(2-methanesulfonyl-ethyl)-piperazine (0.75 mmol, 5.0 eq), CuI (0.15 mmol, 1 eq), L-proline (0.27 mmol, 1.8 eq), and potassium carbonate (0.15 mmole, 1 eq) in DMSO (2 mL) was heated at 120° C. for 1 hour under microwave conditions. The crude was purified through prep-LCMS 5–95% to provide Compound A223 as a brown sticky oil (5 mg, 6%). Exact mass calculated for C28H39N7O5S 585.3, found LCMS (ESI) m/z 586.6 (M+H+, 90%).

Workup

  1. customThe crude was purified through prep-LCMS 5–95%

Sources & evidence

ORD record
ord-ba9bf7c75ee14ecdb4a7d446cea794e8
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Reaction notes

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