Sodium hydride → HCID 59485871, compound

HRID 1972282Notes

Reaction equation

HRID 1972282 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:11][NH:10][C:9]2=[O:23])=[CH:4][CH:3]=1.FC(F)(F)C1C=CC=C(C=C)C=1.[H-].[Na+].Cl[CH2:39][C:40]1[N:44]=[C:43]([C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)[O:42][N:41]=1>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:14]=3)[CH2:11][N:10]([CH2:39][C:40]3[N:44]=[C:43]([C:45]4[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=4)[O:42][N:41]=3)[C:9]2=[O:23])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 5209863-(Trifluoromethyl)styreneHCID 27971313-(Chloromethyl)-5-(4-methoxyphenyl)-1,2,4-oxadiazoleHCID 59485598HCID 59485598, compound

Product 1

HCID 59485871HCID 59485871, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of (S)-1-(4-chlorophenyl)-5-(3-(trifluoromethyl)phenyl)imidazolidin-2-one (40 mg, 0.117 mmol, prepared by following the same procedure as described in example 151 using 1-(trifluoromethyl)-3-vinylbenzene as the starting material.) in anhydrous DMF (2 mL) is cooled down to 0° C. in an ice bath when NaH (17 mg, 60% in mineral oil, 0.423 mmol) is added into the solution portion wise. After the addition, the mixture is stirred at 0° C. for 10 min when a solution of 3-(chloromethyl)-5-(4-methoxyphenyl)-1,2,4-oxadiazole (31.6 mg, 0.141 mmol) in DMF (1 mL) is added into the mixture. The resulted mixture is allowed to warm up to room temperature and stir for 1 h. The residue is purified by preparatory LC/MS to provide the title compound; 1H NMR (CD3OD, 400 MHz) δ 7.95 (d, J=9.2 Hz, 2H), 7.62 (s, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.48-7.39 (m, 2H), 7.31 (d, J=9.2 Hz, 2H), 7.13 (d, J=8.8 Hz, 2H), 7.00 (d, J=8.8 Hz, 1H), 5.50 (dd, J=9.2, 6.0 Hz, 1H), 4.68 (m, 2H), 4.07 (t, J=9.2 Hz, 1H), 3.78 (s, 3H), 3.41 (dd, J=9.0, 6.0 Hz, 1H); HPLC-MS calculated for C26H21ClF3N4O3 (M+H+) 529.1, found 529.0.

Workup

  1. additionis added into the solution portion wise
  2. additionAfter the addition
  3. additionis added into the mixture
  4. customThe residue is purified by preparatory LC/MS

Sources & evidence

ORD record
ord-4b2595ffc0e24ac0ba46bdceab02740c
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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