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

HRID 2279786Notes

Reaction equation

HRID 2279786 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([Cl:35])C(Br)=CC=1>>[NH2:1][C:2]1[C:3]([C:4]([NH:6][CH3:7])=[O:5])=[C:11]([Cl: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 866977366-amino-3-bromo-2-chloro-N-methylbenzamide2×

Product 1

HCID 866977356-amino-2-chloro-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylbenzamideYield 33%

Procedure

Prepared analogously to Compound 3C replacing compound 3D with 6-amino-3-bromo-2-chloro-N-methylbenzamide (Compound 28D, 700 mg, 2.66 mmol) and to afford 274 mg of the title compound (33%). 1H NMR (400 MHz, CD3OD) δ=7.87 (s, 1H), 7.68 (s, 1H), 7.25 (d, J=8.6 Hz, 1H), 6.73 (d, J=8.6 Hz, 1H), 4.27 (t, J=7.0 Hz, 2H), 3.55 (t, J=6.2 Hz, 2H), 2.92 (s, 3H), 2.06 (quin, J=6.5 Hz, 2H). MS (ESI): m/z=309.10 [M+H]+. UPLC: tR=0.81 min (UPLC-TOF: polar—3 min).

Sources & evidence

ORD record
ord-81ac115c86e249c3b4b1128ef29419f3
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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