Acetonitrile → HCID 71204698, compound

HRID 712882Notes

Reaction equation

HRID 712882 reaction equation
[C@@H:1]12[CH2:6][C@@H:5]1[CH2:4][C@H:3]([C:7]([NH:9][C:10]1([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=3)[CH2:12][CH2:11]1)=[O:8])[NH:2]2.CC#N.[F:26][C:27]([F:37])([F:36])[C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1>>[F:26][C:27]([F:36])([F:37])[C:28]1[CH:35]=[CH:34][C:31]([CH2:32][N:2]2[C@@H:3]([C:7]([NH:9][C:10]3([C:13]4[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=4)[CH2:11][CH2:12]3)=[O:8])[CH2:4][C@@H:5]3[C@H:1]2[CH2:6]3)=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 71186368HCID 71186368, compound

Product 1

HCID 71204698HCID 71204698, compoundYield 92.2%

Procedure

To a solution of methyl 4-(1-((1R,3R,5R)-2-azabicyclo[3.1.0]hexane-3-carboxamido)cyclopropyl)benzoate (D104) (1.7 g, 5.7 mmol) in MeCN (80 ml) Cs2CO3 (2.8 g, 8.5 mmol) and 4-(trifloromethyl)benzylbromide (1.6 g, 6.8 mmol) were added and the resulting mixture was stirred at RT for 4 hrs. Solvent was evaporated and the residue was loaded on a SNAP-Si cartridge (100 g), eluted with a mixture DCM/AcOEt from 10/0 to DCM/AcOEt 9/1. Collected fractions after solvent evaporation afforded the title compound (D147) (2.41 g).

Workup

  1. customSolvent was evaporated
  2. washeluted with a mixture DCM/AcOEt from 10/0 to DCM/AcOEt 9/1
  3. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-dfa6b88e14334153affb945fc95c0be2
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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