Ether hydrochloride → HCID 69764041, compound

HRID 1063992Notes

Reaction equation

HRID 1063992 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[C:23]2[CH3:27])[CH3:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.CCOCC>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[C:23]2[CH3:27])[CH3:13])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 60045104HCID 60045104, compound

Product 1

HCID 69764041HCID 69764041, compoundYield 125.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-chloro-N-(2,5-difluorophenyl)-N-((1R)-1-{2-[2-(2-methyl-1H-imidazol-1-yl)ethyl]phenyl}ethyl)benzenesulfonamide (39 mg, 0.075 mmol) was dissolved in CH2Cl2 (2.0 mL) and treated with HCl—Et2O solution (1.0 M, 83 μL) at 25° C. for 15 min. Solvents were removed in vacuo and chromatography afforded 4-chloro-N-(2,5-difluorophenyl)-N-((1R)-1-(2-[2-(2-methyl-1H-imidazol-1-yl)ethyl]phenyl}ethyl)benzenesulfonamide hydrochloride (26 mg, 61%) as white solid: m.p. 190.5-192.0° C.; Rf 0.38 (10:1, CH2Cl2-methanol); 1H NMR (CD3OD, 300 MHz) δ 7.39-7.67 (m, 5H), 7.29 (m, 1H), 6.18-7.12 (m, 7H), 5.67 (q, 1H, J=6.9 Hz), 4.44 (m, 1H), 4.35 (m, 1H), 3.59 (m, 1H), 3.25 (m, 1H), 2.27 (m, 3H), 1.31 (d, 3H, I=6.6 Hz); LCMS 3.07 min, m/z 516.05 (M+H+−HCl, C26H24ClF2N3O2S HCl requires 516.00).

Workup

  1. customSolvents were removed in vacuo and chromatography

Sources & evidence

ORD record
ord-b8e31b11414c46b3a352ed0779c5a4b2
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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