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

HRID 2279781Notes

Reaction equation

HRID 2279781 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)=[CH:11][C:3]=1[C:4]([N:6](CC)[CH2:7]C)=[O:5].NC1C(C(NC)=O)=C([F:35])C(Br)=CC=1>>[NH2:1][C:2]1[C:3]([C:4]([NH:6][CH3:7])=[O:5])=[C:11]([F:35])[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 866977326-amino-3-bromo-2-fluoro-N-methylbenzamide2×

Product 1

HCID 866977316-amino-2-fluoro-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylbenzamideYield 34%

Procedure

Prepared analogously to Compound 3C replacing Compound 3D with 6-amino-3-bromo-2-fluoro-N-methylbenzamide (Compound 27D, 700 mg, 2.83 mmol) to afford 281 mg of the title compound (34%). 1H NMR (400 MHz, CD3OD) δ=7.88 (d, J=1.8 Hz, 1H), 7.76 (d, J=1.0 Hz, 1H), 7.38 (t, J=8.6 Hz, 1H), 6.59 (d, J=8.6 Hz, 1H), 4.26 (t, J=7.0 Hz, 2H), 3.54 (t, J=6.2 Hz, 2H), 2.92 (s, 3H), 1.98-2.13 (m, 2H). MS (ESI): m/z=293.87 [M+H]+. UPLC: tR=0.60 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-5b323dd7b0ed425a9d4e24241ed9554c
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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