Hydrochloric Acid → HCID 46893052, compound

HRID 15009Notes

Reaction equation

HRID 15009 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:26][C:27]2[N:32]=[C:31]([NH2:33])[CH:30]=[CH:29][CH:28]=2)[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:11][CH:12]=1.Cl>C(OCC)C.C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH2:26][C:27]2[N:32]=[C:31]([NH2:33])[CH:30]=[CH:29][CH:28]=2)[C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:17][CH:18]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 115325276-[2-(2-Chlorophenyl)-5-(4-phenoxyphenyl)pyrrol-1-ylmethyl]pyridin-2-ylamine

Product 1

HCID 46893052HCID 46893052, compoundYield 153.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 6-[2-(2-chlorophenyl)-5-(4-phenoxyphenyl)pyrrol-1-ylmethyl]pyridin-2-ylamine (0.071 g, 0.16 mmol) and HCl (0.16 mL of a 1.0 M solution in diethyl ether, 0.16 mmol) in ethanol (3 mL) was stirred at room temperature for 8 h. The mixture was concentrated and purified by trituration with ether to afford the title compound, (0.060 g, 78%) as a pale yellow solid: Rf 0.22 (1:3 ethyl acetate/hexanes); mp 145-148° C.; 1H NMR (300 MHz, CD3OD) δ 7.64 (dd, J=7.4, 1.4 Hz, 1H), 7.48 (d, J=7.4 Hz, 1H), 7.40-7.27 (m, 7H), 7.13 (t, J=7.4 Hz, 1H), 7.02-6.98 (m, 4H), 6.68 (d, J=8.8 Hz, 1H), 6.39 (d, J=3.6 Hz, 1H), 6.34 (d, J=3.6 Hz, 1H), 5.86 (d, J=7.3 Hz, 1H), 5.14 (s, 2H); IR (ATR) 3081, 1660, 1481, 1231 cm−1; ESI MS m/z 452 [C28H22ClN3O+H]+; HPLC (Method 1) 98.6% (AUC), tR=14.99 min. Anal. Calcd for C28H22ClN3O.HCl.0.25H2O: C, 68.23; H, 4.60; N, 8.52. Found: C, 68.29; H, 4.79; N, 8.34.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by trituration with ether

Sources & evidence

ORD record
ord-81d7eb3e428e42e8abfdf4997a53f72b
Source dataset
uspto-grants-2010_06
Patent number
US07732457B2

Reaction notes

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