Sodium Hydroxide → 1-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-6-methyl-4-trifluoromethyl-1H-pyrimidin-2-one

HRID 1891377Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])=[CH:4][C:3]=1[NH:22][C:23]([NH2:25])=[O:24].[F:26][C:27]([F:35])([F:34])[C:28](=O)[CH2:29][C:30](=O)[CH3:31].[OH-].[Na+]>OS(O)(=O)=O.CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]2=3)(=[O:10])=[O:9])=[CH:4][C:3]=1[N:22]1[C:30]([CH3:31])=[CH:29][C:28]([C:27]([F:35])([F:34])[F:26])=[N:25][C:23]1=[O:24]

Participants

Conditions

Temperature: 80 °C

Procedure

To [2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-urea (38 mg, 0.1 mmol) in 13% (v/v) H2SO4 in EtOH was added 1,1,1-trifluoro-2,4-pentanedione (15 μL, 0.15 mmol). The mixture was heated at 80° C. for 6 hrs, followed by neutralization with 6N NaOH solution. Purification by prep. LCMS yielded 1-[2-chloro-5-(2,3,4,5-tetrahydro-benzo[b]azepine-1-sulfonyl)-phenyl]-6-methyl-4-trifluoromethyl-1H-pyrimidin-2-one 13-1. MS: 497.7 (M+H)+; tR=8.14 min (method 2).

Workup

customPurification by prep

Sources & evidence

ORD record: ord-ae34498e48374967985c3a82645ff36f
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507536B2

Reaction notes

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