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

HRID 2279734Notes

Reaction equation

HRID 2279734 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]3[C:11]=2[CH2:12][N:13](C)[C:14]3=[O:22])[CH:7]=[N:6]1.NC1C=CC(Br)=CC=1C(NC)=O>>[NH2:19][C:16]1[CH:17]=[CH:18][C:10]([C:8]2[CH:7]=[N:6][N:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:9]=2)=[CH:11][C:15]=1[C:14]([NH:13][CH3:12])=[O:22]

Participants

3

Reactant 2

HCID 509995112-Amino-5-bromo-N-methylbenzamide2×HCID 672550944-[1-(3-Hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-7-nitro-2,3-dihydro-1H-isoindol-1-one

Product 1

HCID 678140542-amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N-methylbenzamideYield 47%

Procedure

Prepared analogously to Compound 1D using 2-amino-5-bromo-n-methyl-benzamide (Compound 87D, 600 mg, 2.62 mmol) to afford 335 mg of the title compound (47%). 1H NMR (400 MHz, CD3OD) δ 7.86 (s, 1H), 7.76 (s, 1H), 7.62 (d, J=2.0 Hz, 1H), 7.38 (dd, J=2.0, 8.3 Hz, 1H), 6.77 (d, J=8.3 Hz, 1H), 4.25 (t, J=6.8 Hz, 2H), 3.54 (t, J=6.2 Hz, 2H), 2.89 (s, 3H), 2.06 (quin, J=6.5 Hz, 2H). MS (ESI): m/z 275.57 [M+H]+. UPLC: tR=0.55 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-3b091d28c1d947ecba937d27f0c969b9
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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