1,2-Dichloroethane → 3-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-N-pyrrolidin-3-ylmethyl-benzamide

HRID 2386356Notes

Reaction equation

HRID 2386356 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=O)[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.C(OC([N:33]1[CH2:37][CH2:36][CH:35]([CH2:38][NH2:39])[CH2:34]1)=O)(C)(C)C.C(Cl)CCl>CN(C=O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([NH:39][CH2:38][CH:35]3[CH2:36][CH2:37][NH:33][CH2:34]3)=[O:22])[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylateHCID 670445203-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

Product 1

HCID 586034573-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-N-pyrrolidin-3-ylmethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate 9 (2.2 mmol) was coupled with 3-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (5 mmol) using EDC (3 mmol) in DMF (20 mL). The DMF was removed by rotary evaporation and the residue purified by flash chromatography on silica gel (ethyl acetate as eluent.) The resulting product was deprotected following procedure G. LC-MS showed the product had the expected M+H+ of 418. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.9 (s, 1H) 8.5-8.75 (m, 2H) 8.3 (m, 1H) 8.0 (d, 1H) 7.65 (m, 1H) 7.3 (m, 1H) 7.05 (m, 2H) 6.68 (d, 2H) 3.6 (m, 2H) 3.4 (m, 2H) 3.2-3.4 (m, 2H) 2.48 (m, 3H) 2.0 (m, 2H) 1.7 (m, 2H).

Workup

  1. customThe DMF was removed by rotary evaporation
  2. customthe residue purified by flash chromatography on silica gel (ethyl acetate as eluent.) The resulting product

Sources & evidence

ORD record
ord-62be7222866f420a892f92863dcea13f
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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