3-Aminopyridine → HCID 58975004, compound

HRID 737057Notes

Reaction equation

HRID 737057 reaction equation
[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([S:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1CN([P+](ON2N=[N:51][C:46]3[CH:47]=[CH:48][CH:49]=[CH:50]C2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:60][C:61]1C=NC=CC=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:1]1([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([S:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([NH:60][CH2:61][C:49]4[CH:50]=[N:51][CH:46]=[CH:47][CH:48]=4)=[O:24])=[CH:25][CH:26]=3)(=[O:17])=[O:16])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58975136HCID 58975136, compound

Product 1

HCID 58975004HCID 58975004, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add to a stirring mixture of 4-(3-cyclopentyl-indole-1-sulfonyl)-benzoic acid (0.188 g, 0.50 m mol), PyBOP (0.0.288 g, 0.50 m mol), and 3-amino-pyridine (0.063 g, 0.59 mmol) in dry CH2Cl2 (10 mL) under N2, Hunigs base (0.148 g, 0.200 mL, 1.11 m mol.). Stir the reaction is overnight at ambient temperature and evaporate on the rotary evaporator. Chromatograph the residue on the ISCO system using a 40 g column and a hexane-EtOAc gradient system (0-100%) to give 0.048 g of the title compound as white foam: Mass spectrum (m/e) (M+H) 460.1697; found 460.1681.

Workup

  1. customevaporate on the rotary evaporator

Sources & evidence

ORD record
ord-6de8ca272e224a0fbd8acb49a70f6dd9
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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