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

HRID 2279717Notes

Reaction equation

HRID 2279717 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=CC(Br)=CC=1C(NC)=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][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 509995112-Amino-5-bromo-N-methylbenzamideHCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

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

Procedure

Prepared analogously to Compound 3C replacing Compound 3D with 2-amino-5-bromo-N-methyl-benzamide (920 mg, 4.0 mmol) to give the title compound as 0.35 g of a white solid (32%, over two steps). 1H NMR (CDCl3+CD3OD, 400 MHz): δ=7.65 (s, 1H), 7.64 (s, 1H), 7.47 (d, J=2.0 Hz, 1H), 7.28 (dd, J=8.4, 2.0 Hz, 1H), 6.69 (d, J=8.4 Hz, 1H), 4.21 (t, J=6.6 Hz, 2H), 3.53 (t, J=5.6 Hz, 2H), 2.90 (s, 3H), 2.00 (m, 2H). MS (ESI): m/z=275.29 [M+H]+. HPLC: tR=2.50 min (ZQ3: polar—5 min).

Sources & evidence

ORD record
ord-83c12659726545d8887f6a1ab343e1d4
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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