3-Aminopyridine → HCID 67023264, compound

HRID 737061Notes

Reaction equation

HRID 737061 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+](O[N:44]2N=[N:51][C:46]3C=[CH:48][CH:49]=[CH:50][C:45]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.N[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:44][C:45]4[CH:46]=[N:51][CH:48]=[CH:49][CH:50]=4)=[O:24])=[C:25]([CH3:61])[CH:26]=3)(=[O:17])=[O:16])[CH:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

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

Product 1

HCID 67023264HCID 67023264, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a mixture of 4-(3-Cyclopentyl-indole-1-sulfonyl)-benzoic acid (0.188 g, 0.50 mmol), 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 add Hunigs base (0.148 g, 0.200 mL, 1.11 mmol). Stir overnight the reaction at ambient temperature and evaporate on the rotary evaporator. Chromatograph the residue on the ISCO using a 40 g column and a hexane-EtOAc gradient system (0-100%) to give 0.048 g of the title compound as a white foam. Mass spectrum (m/e) (M+H) 460.1697; found 460.1681.

Workup

  1. stirringStir overnight
  2. customthe reaction at ambient temperature
  3. customevaporate on the rotary evaporator

Sources & evidence

ORD record
ord-1a2cb70b59c34ef6b3f1088889e4ce05
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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