2-Mercaptoethanol → HCID 59856812, compound

HRID 2377920Notes

Reaction equation

[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([CH3:20])=[C:18]([O:21][C:22]3[C:23]([CH3:29])=[N:24][C:25](Cl)=[CH:26][CH:27]=3)[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[SH:36][CH2:37][CH2:38][OH:39]>>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([CH3:20])=[C:18]([O:21][C:22]3[C:23]([CH3:29])=[N:24][C:25]([S:36][CH2:37][CH2:38][OH:39])=[CH:26][CH:27]=3)[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 15672-Mercaptoethanol

HCID 11430Potassium Carbonate

HCID 59856760HCID 59856760, compound

Product 1

HCID 59856812HCID 59856812, compoundYield 2%

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-[6-(6-chloro-2-methyl-pyridin-3-yloxy)-5-methyl-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (835 mg, 1.98 mmol) and potassium carbonate (305 mg, 2.2 mmol) in 3 mL of 2-mercapto-ethanol was stirred in microwave at 80° C. After 17 hours, mixture was continued to be stirred at 100° C. for 30 minutes and then 120° C. for 30 minutes. Mixture was purified by HPLC and column chromatography (hexane/AcOEt) to give Compound C12 as a white solid (16.4 mg, 2%). 1H NMR (CDCl3, 400 MHz) δ 1.07-1.09 (d, J=6.3 Hz, 6H), 1.68-1.78 (m, 2H), 1.90-1.99 (m, 2H), 2.12 (s, 3H), 2.29 (s, 3H), 3.23-3.25 (t, J=5.1 Hz, 2H), 3.32-3.38 (m, 2H), 3.68-3.71 (m, 2H), 3.91-3.94 (t, J=4.9 Hz, 2H), 4.84-4.90 (m, 1H), 5.24-5.30 (m, 1H), 7.12-7.21 (m, 2H), 8.12 (s, 1H). Exact mass calculated for C22H30N4O5S 462.19, found 463.3 (MH+).

Workup

stirringto be stirred at 100° C. for 30 minutes
wait120° C. for 30 minutes
customMixture was purified by HPLC and column chromatography (hexane/AcOEt)

Sources & evidence

ORD record: ord-8ef84ccd022c449493e5ca3e8a4b7532
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470699B2

Reaction notes

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