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

HRID 2250384Notes

Reaction equation

HRID 2250384 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]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)=[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]([C:40]2[CH:41]=[CH:42][C:43]([Cl:46])=[CH:44][CH:45]=2)=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 68465037N-[2-Amino-5-(4-chloro-phenyl)-pyridin-3-yl]3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propionamide2×

Product 1

HCID 68466161N-[2-Amino-5-(4-chloro-phenyl)-pyridin-3-yl]-3-(6-amino-4-methyl-pyridin-2-yl)-propionamideYield 14.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

405 mg of N-[2-amino-5-(4-chloro-phenyl)-pyridin-3-yl]-3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propionamide (compound B8) are dissolved in 24 ml of aqueous acetic acid (50% strength) and heated at 80° C. for 3 h. Subsequent workup according to the procedure described herein for example B5 yields 36 mg of the title compound as an oil. ESI-MS: 382.2/384.2 (MH+, 100%/360%). TLC: Rf=0.40 (dichloromethane/methanol 10:1).

Sources & evidence

ORD record
ord-6cfb2954311d4948b3110e655d882df6
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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