Toluene → HCID 71257219, compound

HRID 710178Notes

Reaction equation

HRID 710178 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[C:19]1[O:20][C:21]2[CH:27]=[CH:26][C:25]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:24][C:22]=2[N:23]=1.[C:34](Cl)(=[O:43])[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[F:8][C:9]1[CH:14]=[C:13]([S:15]([CH3:18])(=[O:16])=[O:17])[CH:12]=[CH:11][C:10]=1[C:19]1[O:20][C:21]2[CH:27]=[CH:26][C:25]([CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:43])[CH2:30][CH2:29]3)=[CH:24][C:22]=2[N:23]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 10387Benzyl chloroformateHCID 71089569HCID 71089569, compound

Product 1

HCID 71257219HCID 71257219, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate (Example 61) (70 mg, 0.14 mmol) dissolved in DCM (10 ml) and added TEA (0.1 ml, 0.72 mmol). This mixture stirred at rt for 30 mins and added benzyl carbonochloridate in toluene (48 mg, 0.28 mmol). After 30 mins reaction mixture quenched with water and extracted with DCM. DCM removed on rotavapour to obtain the crude. Crude was purified by combiflash using EtOAc and Petether (1:2) as eluent to afford the titled compound (30 mg) as an off-white solid. M.P.: 172-175° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.49-8.43 (m, 1H), 7.90-7.84 (m, 2H), 7.68 (d, J 1.4, 1H), 7.57 (d, J 8.5, 1H), 7.42-7.22 (m, 6H), 5.17 (s, 2H), 4.42-4.25 (bs, 2H), 3.13 (s, 3H), 3.00-2.78 (m, 3H), 2.00-1.88 (m, 2H), 1.80-1.65 (m, 2H).

Workup

  1. customAfter 30 mins reaction mixture
  2. customquenched with water
  3. extractionextracted with DCM
  4. customDCM removed on rotavapour
  5. customto obtain the crude
  6. customCrude was purified by combiflash

Sources & evidence

ORD record
ord-e80ea6385aff43b8a97474c7c25d00f9
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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