Potassium Carbonate → HCID 70872590, compound

HRID 73054Notes

Reaction equation

HRID 73054 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:25][O:24][C:5]2([CH2:10][CH2:9][N:8]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=3)=[O:12])[CH2:7][CH2:6]2)[CH2:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]1[N:39]=[CH:38][CH:37]=[CH:36][N:35]=1>CS(C)=O>[ClH:33].[CH3:26][C:2]1([CH3:1])[N:3]([C:34]2[N:39]=[CH:38][CH:37]=[CH:36][N:35]=2)[CH2:4][C:5]2([CH2:6][CH2:7][N:8]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([CH3:23])[CH:14]=3)=[O:12])[CH2:9][CH2:10]2)[O:24][CH2:25]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 66548351(9,9-Dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone

Product 1

HCID 70872590HCID 70872590, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (11.0 mg, 0.0305 mmol), potassium carbonate (4.2 mg, 0.031 mmol) and 2-chloropyrimidine (3.7 mg, 0.031 mmol) in DMSO (90 μL) was heated at 90° C. for 2 h. The reaction was filtered and purified by HPLC (1-99% CH3CN/5 mM HCl) to provide (3,3-dimethyl-4-(pyrimidin-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)(4-isopropoxy-3-methylphenyl)methanone hydrochloride (6.0 mg, 0.012 mmol, 38%). ESI-MS m/z calc. 438.3. Found 439.3 (M+1)+; Retention time: 1.92 minutes (3 min run).

Workup

  1. filtrationThe reaction was filtered
  2. custompurified by HPLC (1-99% CH3CN/5 mM HCl)

Sources & evidence

ORD record
ord-6331b6f1842d4c5ea97219bb8787570d
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

Loading…