3-Aminopyridine → HCID 69565915, compound

HRID 1178992Notes

Reaction equation

HRID 1178992 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(O)=O)=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1CN([P+]([O:43]N2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.N[C:61]1[CH:62]=[N:63][CH:64]=[CH:65][CH:66]=1.C[CH2:68][N:69]([CH:73](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][CH:21]=[CH:25][C:26]=3[C:68]([NH:69][CH2:73][C:61]3[CH:62]=[N:63][CH:64]=[CH:65][CH:66]=3)=[O:43])(=[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 69565915HCID 69565915, 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-ce7353c7e13a4f07b6c6bce2f658633c
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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