2-Amino-5-bromo-N-methylbenzamide → 2-Amino-5-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-N-methylbenzamide

HRID 2279745Notes

Reaction equation

HRID 2279745 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]O)[CH:19]=2)=[CH:11][C:3]=1[C:4]([N:6]([CH2:9]C)CC)=[O:5].NC1C=CC(Br)=CC=1[C:27](NC)=[O:28].CC1(C)C(C)(C)OB(C2C=NN(CCCCO)C=2)O1>>[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][CH2:27][OH:28])[CH:19]=2)=[CH:11][C:3]=1[C:4]([NH:6][CH3:9])=[O:5]

Participants

4

Reactant 3

HCID 509995112-Amino-5-bromo-N-methylbenzamide2×HCID 678147924-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-olHCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 678124652-Amino-5-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-N-methylbenzamideYield 17%

Procedure

Prepared analogously to Compound 3C using 2-amino-5-bromo-n-methyl-benzamide (Compound 8D, 300 mg, 1.31 mmol) and 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-ol (Compound 14C, 383 mg, 1.44 mmol) to afford 64 mg of the title compound (17%). 1H NMR (400 MHz, CDCl3) δ 7.67 (s, 1H), 7.54 (s, 1H), 7.40 (d, J=2.0 Hz, 1H), 7.32 (dd, J=2.0, 8.6 Hz, 1H), 6.71 (d, J=8.3 Hz, 1H), 6.13 (br. s., 1H), 5.43 (br. s., 2H), 4.20 (t, J=6.9 Hz, 2H), 3.65-3.72 (m, 2H), 3.01 (d, J=5.1 Hz, 3H), 2.01 (quin, J=7.3 Hz, 2H), 1.58-1.67 (m, 3H).

Sources & evidence

ORD record
ord-78aca5222e604fa9aa98419560da2d48
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

Loading…