Hydrochloric Acid → 6-[2-(2-Chloro-phenyl)-5-(4-propoxy-phenyl)-pyrrol-1-ylmethyl]-pyridin-2-ylamine hydrochloride

HRID 15008Notes

Reaction equation

HRID 15008 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:23][C:24]2[N:29]=[C:28]([NH2:30])[CH:27]=[CH:26][CH:25]=2)[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)=[CH:11][CH:12]=1.Cl>C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:23][C:24]2[N:29]=[C:28]([NH2:30])[CH:27]=[CH:26][CH:25]=2)[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[CH:15][CH:14]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 116760686-((2-(2-chlorophenyl)-5-(4-propoxyphenyl)-1H-pyrrol-1-yl)methyl)pyridin-2-amine

Product 1

HCID 468929316-[2-(2-Chloro-phenyl)-5-(4-propoxy-phenyl)-pyrrol-1-ylmethyl]-pyridin-2-ylamine hydrochlorideYield 176.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 6-[2-(2-chloro-phenyl)-5-(4-propoxy-phenyl)-pyrrol-1-ylmethyl]-pyridin-2-ylamine (50.0 mg, 0.12 mmol) and HCl (0.06 mL of a 2.0 M solution in diethyl ether, 0.12 mmol) in diethyl ether (10 mL) was stirred at room temperature for 30 min. The mixture was concentrated and the solid obtained triturated with hexanes to afford the title compound (48.0 mg g, 88%) as an off-white solid: Rf 0.65 (50:50 hexanes/ethyl acetate); mp 68-76° C.; 1H NMR (300 MHz, CDCl3) δ 7.20-7.60 (m, 7H), 6.89 (d, J=8.7 Hz, 2H), 6.65 (br s, 1H), 6.45 (d, J=8.2 Hz, 1H), 6.39 (d, J=3.6 Hz, 1H), 6.35 (d, J=3.6 Hz, 1H), 5.75 (d, J=8.2 Hz, 1H), 5.24 (s, 2H), 3.93 (t, J=6.6 Hz, 2H), 1.80 (tq, J=7.5, 6.6 Hz, 2H), 1.04 (t, J=7.5 Hz, 3H); IR (ATR) 3292, 3105, 2964, 2711, 1661, 1628, 1486, 1244, 1174, 833, 755, 722 cm−1; ESI MS m/z 418 [C25H24ClN3O+H]+; HPLC (Method 1) 97.1% (AUC), tR=14.53 min. Anal. Calcd for C25H24ClN3O.HCl.0.5H2O: C, 64.80; H, 5.66; N, 9.07. Found: C, 64.63; H, 5.50; N, 8.65.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe solid obtained
  3. customtriturated with hexanes

Sources & evidence

ORD record
ord-85a80ec6d3c345dc8e472949dedaf8cc
Source dataset
uspto-grants-2010_06
Patent number
US07732457B2

Reaction notes

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