Sodium Iodide → N, N-dimethyl-2-(4-{2-[(S)-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-2-trifluoromethyl-2,3-dihydro-5H-imidazo[1,2-a]pyrimidin-1-yl]ethyl}phenoxy)acetamide

HRID 633761Notes

Reaction equation

HRID 633761 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[C:20]3=[N:21][C:22]([N:26]4[CH2:32][CH:31]5[O:33][CH:28]([CH2:29][CH2:30]5)[CH2:27]4)=[CH:23][C:24](=[O:25])[N:19]3[CH2:18][C@@:17]2([CH3:38])[C:34]([F:37])([F:36])[F:35])=[CH:10][CH:9]=1.Cl[CH2:40][C:41]([N:43]([CH3:45])[CH3:44])=[O:42].[I-].[Na+]>CN(C=O)C>[CH3:44][N:43]([CH3:45])[C:41](=[O:42])[CH2:40][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:16]2[C:20]3=[N:21][C:22]([N:26]4[CH2:27][CH:28]5[O:33][CH:31]([CH2:30][CH2:29]5)[CH2:32]4)=[CH:23][C:24](=[O:25])[N:19]3[CH2:18][C@@:17]2([CH3:38])[C:34]([F:37])([F:36])[F:35])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 72709217(S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Product 1

HCID 73050998N, N-dimethyl-2-(4-{2-[(S)-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-2-trifluoromethyl-2,3-dihydro-5H-imidazo[1,2-a]pyrimidin-1-yl]ethyl}phenoxy)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

235 mg (0.72 mmol) of cesium carbonate are added to a solution of 130 mg (0.29 mmol) of (S)-1-[2-(4-hydroxyphenyl)ethyl]-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one in 10 mL of DMF. After heating at 80° C. for 20 minutes, 52.60 mg (0.43 mmol) of 2-chloro-N,N-dimethylacetamide and 43.30 mg (0.29 mmol) of sodium iodide are added. The reaction medium is heated at 80° C. overnight. The reaction medium is evaporated to dryness. After purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 25 min 10% B, t 30 min 10% B), 138 mg of N,N-dimethyl-2-(4-{2-[(S)-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-2-trifluoromethyl-2,3-dihydro-5H-imidazo[1,2-a]pyrimidin-1-yl]ethyl}phenoxy)acetamide were obtained, corresponding to the following characteristics:

Workup

  1. temperatureThe reaction medium is heated at 80° C. overnight
  2. customThe reaction medium is evaporated to dryness
  3. customAfter purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 25 min 10% B, t 30 min 10% B), 138 mg of N,N-dimethyl-2-(4-{2-[(S)-2-methyl-7-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-5-oxo-2-trifluoromethyl-2,3-dihydro-5H-imidazo[1,2-a]pyrimidin-1-yl]ethyl}phenoxy)acetamide
  4. customwere obtained, corresponding to the following characteristics

Sources & evidence

ORD record
ord-8aafc310e0114d4694229fd7a3a92c3b
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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