2-amino-5-bromo-N-methoxybenzamide → 2-amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methoxybenzamide

HRID 2279777Notes

Reaction equation

HRID 2279777 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)CC)=[O:5].NC1C=CC(Br)=CC=1[C:27](NOC)=[O:28]>>[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][O:28][CH3:27])=[O:5]

Participants

3

Reactant 2

HCID 816791802-amino-5-bromo-N-methoxybenzamide2×HCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 866977282-amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methoxybenzamideYield 14%

Procedure

Prepared analogously to Compound 3C replacing Compound 3D with 2-amino-5-bromo-N-methoxybenzamide (Compound 26D, 1 g, 4.08 mmol) to afford 169 mg of the title compound (14%). 1H NMR (400 MHz, CD3OD) δ=7.85 (d, J=0.5 Hz, 1H), 7.74 (d, J=0.8 Hz, 1H), 7.54 (d, J=2.0 Hz, 1H), 7.41 (dd, J=2.2, 8.5 Hz, 1H), 6.79 (d, J=8.6 Hz, 1H), 4.25 (t, J=7.0 Hz, 2H), 3.81 (s, 3H), 3.54 (t, J=6.2 Hz, 2H), 2.06 (t, J=6.4 Hz, 2H). MS (ESI): m/z=291.13 [MH]. UPLC: tR=0.85 min (UPLC-TOF: polar—3 min).

Sources & evidence

ORD record
ord-c87859e04e6d417b8e5871da3f62ccf3
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

Loading…