Ethylamine hydrochloride → HCID 54575465, compound

HRID 1519244Notes

Reaction equation

HRID 1519244 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21][O:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=2)=[N:6][CH:7]=1.Cl.[CH2:33]([NH2:35])[CH3:34].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21][O:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([NH:35][CH2:33][CH3:34])=[O:29])=[CH:25][CH:24]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67468592HCID 67468592, compound

Product 1

HCID 54575465HCID 54575465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)benzoic acid (0.48 g, 1.05 mmol), ethylamine hydrochloride (0.09 g, 1.05 mmol) and DIPEA (0.55 ml, 3.15 mmol) in 9 mL of DMF was added BOP (0.56 g, 1.26 mmol). It was stirred at room temperature for 2 h. Water was added and extracted with EA. The organic layers were combined and washed with 3M LiCl (3×), dried over Na2SO4, filtered and concentrated. The reaction was purified by flash chromatography (silica, 30-70% EtOAc/hexanes) to give 4-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)-N-ethylbenzamide: 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=2.5 Hz, 1H), 8.08 (m, 2H), 7.66 (d, J=8.7 Hz, 2H), 7.48 (dd, J=8.4, 2.6 Hz, 1H), 7.15 (m, 2H), 6.96 (m, 3H), 5.95 (s, 1H), 5.15 (s, 2H), 3.45 (m, 2H), 1,22 (t, J=7.3 Hz, 3H); HRMS exact mass calc for C24H19ClFN3O3S [M+H]+: 484.0892; observed: 484.0900.

Workup

  1. extractionextracted with EA
  2. washwashed with 3M LiCl (3×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe reaction was purified by flash chromatography (silica, 30-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-749334603a09418fba6c99c673d99d54
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

Loading…