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1,2-Dichloroethane → N-(3-Amino-propyl)-3-{2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzamide

HRID 14760
Notes
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Reaction equation

HRID 14760 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](O)=[O:21])[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.C(OC(=O)[NH:32][CH2:33][CH2:34][CH2:35][NH2:36])(C)(C)C.C(Cl)CCl>CN(C=O)C>[NH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][CH:25]=[C:17]([C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)[N:16]=2)[CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 670445203-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

Product 1

HCID 58603495N-(3-Amino-propyl)-3-{2-[2-(4-hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzamide

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

Intermediate 9 (1 mmol) was coupled with (3-Amino-propyl)-carbamic acid tert-butyl ester (3 mmol) using EDC (2 mmol) in DMF (10 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 392. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.68 (s, 1H) 8.35-8.5 (m, 3H) 8.1 (d, 1H) 7.7 (m, 1H) 7.48 (d, 1H) 7.2 (d, 2H) 6.68 (d, 2H) 3.8 (m, 2H) 3.55 (m, 2H) 3.05 (m, 2H) 2.9 (m, 4H) 2.0 (t, 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-6a6078c840e8424e94bf329d6e72dd1c
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732444B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes