3-Amino-6-bromo-N-methylpicolinamide → 3-amino-6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

HRID 2279749Notes

Reaction equation

HRID 2279749 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([NH:11][CH3:12])=[O:10])=[N:4][C:5](Br)=[CH:6][CH:7]=1.NC1C(C(OCC)=O)=NC([C:20]2[CH:21]=[N:22][N:23]([CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:24]=2)=CC=1>>[NH2:1][C:2]1[C:3]([C:9]([NH:11][CH3:12])=[O:10])=[N:4][C:5]([C:20]2[CH:21]=[N:22][N:23]([CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:24]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 866976863-Amino-6-bromo-N-methylpicolinamideHCID 86697704ethyl 3-amino-6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]pyridine-2-carboxylate2×

Product 1

HCID 866977033-amino-6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamideYield 98%

Procedure

Prepared analogously to Compound 6D using ethyl 3-amino-6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]pyridine-2-carboxylate (Compound 15D, 0.211 g, 0.69 mmol) to afford 196 mg of the title compound (98%). 1H NMR (400 MHz, CDCl3) δ 8.12 (br. s., 1H), 7.87 (s, 1H), 7.81 (s, 1H), 7.36 (d, J=8.6 Hz, 1H), 7.03 (d, J=8.6 Hz, 1H), 5.94 (br. s., 2H), 4.23 (t, J=6.9 Hz, 2H), 3.70 (q, J=5.9 Hz, 2H), 3.03 (d, J=5.1 Hz, 3H), 2.03 (quin, J=7.3 Hz, 2H), 1.60-1.67 (m, 3H).

Sources & evidence

ORD record
ord-622cf73d9f874061afd56b4066ea34be
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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