Hydrochloric Acid → HCID 71280824, compound

HRID 1397400Notes

Reaction equation

HRID 1397400 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]([N:16]([CH3:18])[CH3:17])[CH2:14][NH2:15])[N:12]=2)=[CH:4][CH:3]=1.[F:19][C:20]([F:36])([F:35])[C:21]1[O:25][N:24]=[C:23]([C:26]2[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=2)[C:29]([OH:31])=[O:30])[N:22]=1.[ClH:37]>O1CCOCC1>[CH3:17][N:16]([CH3:18])[CH:13]([C:11]1[N:12]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:9][CH:10]=1)[CH2:14][NH:15][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][CH:34]=[C:26]([C:23]2[N:22]=[C:21]([C:20]([F:36])([F:35])[F:19])[O:25][N:24]=2)[CH:27]=1.[ClH:37].[CH3:17][N:16]([CH3:18])[CH:13]([C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:9][CH:10]=1)[CH2:14][NH:15][C:29](=[O:31])[C:28]1[CH:32]=[CH:33][CH:34]=[C:26]([C:23]2[N:22]=[C:21]([C:20]([F:19])([F:36])[F:35])[O:25][N:24]=2)[CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 251808543-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acidHCID 67324358HCID 67324358, compound

Product 2

HCID 69949356HCID 69949356, compoundHCID 71280824HCID 71280824, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(2-(dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide was synthesized from 1-(2-(4-fluorophenyl)oxazol-4-yl)-N1,N1-dimethylethane-1,2-diamine and 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoic acid as described in example 8 step 6. The free base was then stirred with HCl in dioxane solution (4 mL) for 0.5 h at 0° C. to room temperature. The reaction mixture was concentrated and triturated with diethyl ether to afford N-(2-(dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)ethyl)-3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzamide hydrochloride (130 mg, yield 16%) as light brown solid. 1H NMR (400 MHz, DMSO-d6) δ 10.39 (br s, 1H), 9.18-9.15 (t, J=5.6 Hz, 1H), 8.55-8.54 (m, 2H), 8.27-8.25 (m, 1H), 8.21-8.19 (m, 1H), 8.11-8.07 (m, 2H), 7.79-7.75 (t, J=7.8 Hz, 1H), 7.45-7.41 (t, J=8.9 Hz, 2H), 4.84-4.81 (t, J=6.1 Hz, 1H), 4.20-4.13 (m, 1H), 3.87-3.82 (m, 1H), 2.87-2.84 (dd, J=6.9 Hz, 5.0 Hz, 6H). MS (ESI) m/z: Calculated for C23H19F4N5O3: 489.14. found: 490.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-a5eec0ce96a342bfa5a57457542f9501
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…