Hydrochloric Acid → HCID 57135628, compound

HRID 1460105Notes

Reaction equation

HRID 1460105 reaction equation
[CH2:1]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7]([C@H:11]([C:19]2[CH:24]=[CH:23][C:22]([S:25](N(C)C3C=CC=CC=3)(=O)=O)=CC=2)[C:12]2[CH:17]=[CH:16][CH:15]=C(O)C=2)[C@@H:6]([CH3:36])[CH2:5]1)[CH:2]=[CH2:3].[OH2:37].[F-].[CH2:39]([N+:41](CC)([CH2:44][CH3:45])[CH2:42]C)[CH3:40].C(#N)C.Cl.[CH2:52]([OH:54])[CH3:53]>>[CH2:1]([N:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C@@H:11]([C:19]2[S:25][CH:22]=[C:23]([C:42]([N:41]([CH2:44][CH3:45])[CH2:39][CH3:40])=[O:37])[CH:24]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:52]([OH:54])[CH:53]=2)[C@H:6]([CH3:36])[CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 5

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 6342AcetonitrileHCID 16211652Tetraethylammonium fluoride hydrateHCID 57264688(+/-)-4-((alphaR*)-alpha-((2S*,5R*)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-methylbenzenesulfonanilide

Product 1

HCID 57135628HCID 57135628, compoundYield 37%

Procedure

The fourth material to elute from the column of Example 48 (870 mg, 1.57 mmol) was deprotected with tetraethylammonium fluoride hydrate as in Example 44. Chromatography over silica gel with acetonitrile gave an off-white glass. 1H-NMR (300 MHz, DMSO-d6): δ 0.90 (d, J=6.0 Hz, 3H); 1.07 (t, J=7.0 Hz, 6H); 1.15 (d, J=5.7 Hz, 3H) 1.74 (m, 1H); 1.97 (m, 1H); 2.35 (m, 2H); 2.60-2.80 (m, 3H); 3.30 (m, 5H); 5.15 (m, 2H); 5.29 (s, 1H); 5.80 (m, 1H); 6.66 (s, 1H); 6.73 (s, 1H); 6.74 (d, J=7.5 Hz, 2H); 7.19 (t, J=7.5 Hz, 1H); 7.56 (s, 1H); 9.45 (s, 1H). The amine was dissolved in ethanol and converted to the monohydrochloride salt by titration to pH 3.8 with ethanolic hydrochloric acid. The solvent was removed by evaporation and the salt was dissolved in dichloromethane, followed by precipitation with diethyl ether to give 280 mg (37%) of a white solid, mp 109°-116° C. Calculated for C25 H35N3O2S HCl 0.5 H2O: C, 61.65; H, 7.66; N, 8.63; Cl, 7.28; S, 6.58. Found: C, 61.58; H, 7.65; N, 8.54; Cl, 7.36; S, 6.53.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe salt was dissolved in dichloromethane
  3. customfollowed by precipitation with diethyl ether

Sources & evidence

ORD record
ord-e48a8338fce841788cddd64ef85598bb
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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