Diisopropylethylamine → 3-Amino-6-methoxy-N-(3,3,3-trifluoro-2-(4-methoxybenzylamino)-2-methylpropyl)-5-(trifluoromethyl)picolinamide

HRID 887845Notes

Reaction equation

HRID 887845 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([OH:16])=O)=[N:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[F:17][C:18]([F:34])([F:33])[C:19]([CH3:32])([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)[CH2:20][NH2:21].CCN(C(C)C)C(C)C>>[NH2:1][C:2]1[C:3]([C:14]([NH:21][CH2:20][C:19]([NH:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)([CH3:32])[C:18]([F:34])([F:33])[F:17])=[O:16])=[N:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 584423203-Amino-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid2×HCID 584423453,3,3-trifluoro-N2-(4-methoxybenzyl)-2-methylpropane-1,2-diamine2×

Product 1

HCID 584423323-Amino-6-methoxy-N-(3,3,3-trifluoro-2-(4-methoxybenzylamino)-2-methylpropyl)-5-(trifluoromethyl)picolinamide

Procedure

The title compound was prepared analogously to Example 1 from 3-amino-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid (Intermediate D) and 3,3,3-trifluoro-N2-(4-methoxybenzyl)-2-methylpropane-1,2-diamine (Intermediate N). DIPEA was used in this reaction. 1H NMR (400 MHz, DMSO-d6) δ 8.27 (1H, m), 7.68 (1H, s), 7.25 (2H, d), 6.83 (2H, d), 6.70 (2H, s), 3.85 (3H, s), 3.75 (2H, m), 3.72 (3H, s), 3.70 (1H, m), 3.47 (1H, m), 2.80 (1H, t), 1.24 (3H, s)

Sources & evidence

ORD record
ord-c796c88c2225446bb668102b5329fdb3
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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