Potassium Carbonate → HCID 11213728, compound

HRID 1766391Notes

Reaction equation

HRID 1766391 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH:18][CH:19]2[CH:26]3[CH:22]([CH2:23][NH:24][CH2:25]3)[CH2:21][CH2:20]2)=[O:17])[CH:6]=[C:7]([C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)[CH:8]=1)[CH3:2].[F:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH:18][CH:19]2[CH:26]3[CH:22]([CH2:23][N:24]([CH2:35][CH2:34][C:31]4[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=4)[CH2:25]3)[CH2:21][CH2:20]2)=[O:17])[CH:6]=[C:7]([C:9]2[N:13]([CH3:14])[N:12]=[N:11][N:10]=2)[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17390106Benzeneethanol, 4-fluoro-, 1-(4-methylbenzenesulfonate)HCID 69412358HCID 69412358, compound

Product 1

HCID 11213728HCID 11213728, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-[3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)-phenyl]-N′-[(3aRS,4RS,6aSR)-octahydrocyclopenta[c]-pyrrol-4-yl]urea (60 mg, 169 μmol), toluene-4-sulfonic acid 2-(4-fluorophenyl)ethyl ester (55 mg, 169 μmol), potassium carbonate (24 mg, 169 μmol) and acetonitrile (1 mL) was heated to reflux. After 15.5 hours, the mixture was cooled to room temperature and concentrated. The residue was purified by flash column chromatography, eluting with 2% methanol/dichloromethane containing 0.2% aqueous ammonia, to provide a white glass (61 mg, 76%). 1H NMR (300 MHz, CDCl3) δ7.75 (s, 1H), 7.27 (s, 2H), 7.23 (m, 2H), 7.08 (s, 1H), 7.04 (m, 2H), 6.24 (broad s, 1H), 4.23 (broad s, 1H), 4.19 (s, 3H), 3.0-2.6 (m, 10H), 2.3-2.1 (m, 2H), 2.05 (m, 1H), 1.8-1.5 (m, 4H), 1.35 (m, 1H), 1.27 (t, J=7 Hz, 3H). Mass spec (ES+) m/z 478.3 (M+H+, 100%)

Workup

  1. temperaturewas heated to reflux
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography
  4. washeluting with 2% methanol/dichloromethane containing 0.2% aqueous ammonia

Sources & evidence

ORD record
ord-e0ad4aadec3d4f318778cd19223e04cf
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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