Cesium carbonate → HCID 71186489, compound

HRID 712875Notes

Reaction equation

HRID 712875 reaction equation
[CH:1]12[CH2:7][CH:6]1[CH2:5][CH:4]([C:8]([NH:10][C:11]1([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)[CH2:13][CH2:12]1)=[O:9])[NH:3][CH2:2]2.C([O-])([O-])=O.[Cs+].[Cs+].[F:30][C:31]([F:41])([F:40])[C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][CH:33]=1>CC#N>[F:30][C:31]([F:40])([F:41])[C:32]1[CH:39]=[CH:38][C:35]([CH2:36][N:3]2[CH:4]([C:8]([NH:10][C:11]3([C:14]4[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=4)[CH2:12][CH2:13]3)=[O:9])[CH2:5][CH:6]3[CH:1]([CH2:7]3)[CH2:2]2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 71186306HCID 71186306, compound

Product 1

HCID 71186489HCID 71186489, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 4-(1-(3-azabicyclo[4.1.0]heptane-4-carboxamido)cyclopropyl)benzoate (racemic mixture) (D100) (155 mg, 0.49 mmol) in dry MeCN (4 ml), Cs2CO3 (241 mg, 0.74 mmol) and 4-(trifluoromethyl)-benzylbromide (0.09 ml, 0.59 mmol) were added in sequence and the resulting mixture was stirred at RT for 4 hrs. The residue obtained after solvent evaporation was loaded on Biotage SNAP-Si column (25 g) eluting with a mixture cHex/EtOAc from 65/35 to 40/60. Collected fractions after solvent evaporation afforded the title compound (D139) (racemic mixture) (215 mg).

Workup

  1. customThe residue obtained
  2. customafter solvent evaporation
  3. washeluting with a mixture cHex/EtOAc from 65/35 to 40/60
  4. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-62b54d0d557841b094b1d886c7fb787e
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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