Isobutanol → HCID 71257433, compound

HRID 710179Notes

Reaction equation

HRID 710179 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[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.[CH2:34](O)[CH:35]([CH3:37])[CH3:36].CCOC(C)=O.O>CN(C=O)C>[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:3]([O:5][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:4])[CH2:30][CH2:29]3)=[CH:24][C:22]=2[N:23]=1

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 22728543Water ethylacetateHCID 71089569HCID 71089569, compound

Product 1

HCID 71257433HCID 71257433, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(piperidin-4-yl)benzo[d]oxazole 2,2,2-trifluoroacetate (Example 61) (140 mg, 0.29 mmol), isobutanol (42 mg, 0.58 mmol), N,N-Carbonyl diimidazole (82 mg, 0.50 mmol) and TEA (0.2 ml, 1.26 mmol) were dissolved in DMF (2.4 ml). Reaction mixture heated to 60° C. for 18 h. Work up (EtOAc/H2O) followed by purification of the crude by column chromatography on 60-120 mesh silica gel using EtOAc and Petether as eluent to afford the titled compound as a white solid. M.P.: 169-173° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.49-8.43 (m, 1H), 7.83-7.90 (m, 2H), 7.69 (d, J 1.4, 1H), 7.58 (d, J 8.5, 1H), 7.30 (dd, J 1.7, 8.5, 1H) 4.42-4.26 (m, 2H), 3.90 (d, J 6.7, 2H), 3.13 (s, 3H), 3.00-2.78 (m, 3H), 2.00-1.88 (m, 3H), 1.80-1.65 (m, 2H), 0.96 (d, J 6.7, 6H).

Workup

  1. customReaction mixture
  2. customfollowed by purification of the crude by column chromatography on 60-120 mesh silica gel

Sources & evidence

ORD record
ord-5cad4e3b172741b58bf6946bab541c44
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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