N-(2-Amino-5-iodo-pyridin-3-yl)-3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propionamide → N-(2-amino-5-iodo-pyridin-3-yl)-3-(6-amino-4-methyl-pyridin-2-yl)-propionamide

HRID 505418Notes

Reaction equation

HRID 505418 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:39])[CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([NH:19]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:13]=2)=[CH:6][C:5]([I:40])=[CH:4][N:3]=1>C(O)(=O)C>[NH2:1][C:2]1[C:7]([NH:8][C:9](=[O:39])[CH2:10][CH2:11][C:12]2[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([NH2:19])[N:13]=2)=[CH:6][C:5]([I:40])=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 68461097N-(2-Amino-5-iodo-pyridin-3-yl)-3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propionamide2×

Product 1

HCID 68462320N-(2-amino-5-iodo-pyridin-3-yl)-3-(6-amino-4-methyl-pyridin-2-yl)-propionamideYield 27.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

672 mg of N-(2-amino-5-iodo-pyridin-3-yl)-3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propion-amide (compound B9) are dissolved in 13 ml of aqueous acetic acid (50% strength) and heated at 80° C. for 4 h. Subsequent workup according to the procedure described herein for example B5 yields 116 mg of the title compound as an oil after chromatography on silica gel (eluent: dichloromethane/methanol 8:1). ESI-MS: 398.0 (MH+). TLC: Rf=0.32 (dichloromethane/methanol 8:1).

Sources & evidence

ORD record
ord-83865f60dc274115a512cda772027700
Source dataset
uspto-grants-2010_08
Patent number
US07781453B2

Reaction notes

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