Sodium Carbonate → HCID 89350913, compound

HRID 712869Notes

Reaction equation

HRID 712869 reaction equation
[CH2:1]1[C:3]2([CH2:8][CH2:7][NH:6][CH:5]([C:9]([NH:11][C@H:12]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[CH3:13])=[O:10])[CH2:4]2)[CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>CC#N>[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][C:34]([CH2:35][N:6]2[CH2:7][CH2:8][C:3]3([CH2:2][CH2:1]3)[CH2:4][CH:5]2[C:9]([NH:11][C@H:12]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([O:20][CH2:35][C:34]3[CH:33]=[CH:32][C:31]([C:30]([F:29])([F:39])[F:40])=[CH:38][CH:37]=3)=[O:19])=[CH:16][CH:15]=2)[CH3:13])=[O:10])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 71186541HCID 71186541, compound

Product 1

HCID 89350913HCID 89350913, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
68 °C

Procedure

To a solution of 4-((1S)-1-(6-azaspiro[2.5]octane-5-carboxamido)ethyl)benzoic acid (D128) (10 mg, 33.1 μmol) in dry MeCN, Na2CO3 (17.5 mg, 165.4 μmol) and 4-(trifluoromethyl)-benzylbromide (24 mg, 99.2 μmol) were added in sequence. The mixture was heated at 68° C. for 18 hrs. The solid was filtered off, MeCN was evaporated and the residue was purified by Biotage SNAP-Si column (10 g) eluting with a mixture DCM/EtOAc from 100/0 to 80/20. Collected fractions after solvent evaporation afforded the title compounds (D129) (14.8 mg).

Workup

  1. filtrationThe solid was filtered off
  2. customMeCN was evaporated
  3. customthe residue was purified by Biotage SNAP-Si column (10 g)
  4. washeluting with a mixture DCM/EtOAc from 100/0 to 80/20
  5. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-0d1591e0cde8455cbcf1cd624085c864
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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