2-Amino-5-bromo-N-ethylbenzamide → 2-amino-N-ethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

HRID 2279736Notes

Reaction equation

HRID 2279736 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][CH3:8])=[O:5].NC1C=CC(Br)=CC=1C(NCC)=O>>[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]([NH:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 187118562-Amino-5-bromo-N-ethylbenzamide2×HCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 866976932-amino-N-ethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamideYield 37%

Procedure

Prepared analogously to Compound 3C replacing Compound 3D with 2-amino-5-bromo-N-ethylbenzamide (Compound 9D, 1.40 g, 5.77 mmol) to afford 729 mg of the title compound (37%). 1H NMR (400 MHz, CD3OD) δ 7.87 (s, 1H), 7.76 (d, J=0.5 Hz, 1H), 7.63 (d, J=2.0 Hz, 1H), 7.34-7.41 (m, 1H), 6.77 (d, J=8.3 Hz, 1H), 4.25 (t, J=6.9 Hz, 2H), 3.54 (t, J=6.2 Hz, 2H), 3.38 (q, J=7.2 Hz, 2H), 2.06 (quin, J=6.6 Hz, 2H), 1.23 (t, J=7.2 Hz, 3H). MS (ESI): m/z 289.32 [M+H]+. UPLC: tR=0.63 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-ec4f3615eb754bfb812aaa0329d6e336
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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