2-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide → 3-amino-6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

HRID 2279726Notes

Reaction equation

HRID 2279726 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][N:18]([CH2:20][CH2:21][CH2:22][OH:23])[CH:19]=2)=C[C:3]=1[C:4]([N:6]([CH2:9]C)CC)=[O:5].[NH2:24]C1C(C(NC)=O)=NC(Br)=CC=1>>[NH2:1][C:2]1[C:3]([C:4]([NH:6][CH3:9])=[O:5])=[N:24][C:12]([C:15]2[CH:16]=[N:17][N:18]([CH2:20][CH2:21][CH2:22][OH:23])[CH:19]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamideHCID 866976863-Amino-6-bromo-N-methylpicolinamide2×

Product 1

HCID 678187943-amino-6-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

Procedure

Prepared analogously to Compound 3C replacing Compound 3D 3-amino-6-bromo-N-methylpyridine-2-carboxamide (Compound 6D 700 mg, 3 mmol) to isolate 386 mg of the title compound as a hygroscopic foam (46%). 1H NMR (400 MHz, CDCl3) δ 8.11 (br. s., 1H), 7.88 (s, 1H), 7.82 (s, 1H), 7.36 (d, J=8.3 Hz, 1H), 7.03 (d, J=8.3 Hz, 1H), 5.95 (br. s., 2H), 4.34 (t, J=6.4 Hz, 2H), 3.68 (q, J=5.8 Hz, 2H), 3.02 (d, J=5.01 Hz, 3H), 2.58 (t, J=5.7 Hz, 1H), 2.11 (td, J=6, 12.3 Hz, 2H).

Sources & evidence

ORD record
ord-3a468580a20a481e83ae2f330eafe78a
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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