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

HRID 2279741Notes

Reaction equation

HRID 2279741 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]([CH2:9]C)[CH2:7]C)=[O:5].NC1C=CC(Br)=CC=1C(N(C)C)=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]([N:6]([CH3:7])[CH3:9])=[O:5]

Participants

3

Reactant 2

HCID 509995122-Amino-5-bromo-N,N-dimethylbenzamide2×HCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 678148032-Amino-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N,N-dimethylbenzamideYield 39%

Procedure

Prepared analogously to Compound 3C replacing Compound 3D with 2-amino-5-bromo-N,N-dimethyl benzamide (Compound 11D, 1.47 g, 6.06 mmol) to afford 689 mg of the title compound (39%). 1H NMR (400 MHz, CD3OD) δ 7.86 (d, J=0.5 Hz, 1H), 7.71 (d, J=0.8 Hz, 1H), 7.36 (dd, J=2.2, 8.5 Hz, 1H), 7.26 (d, J=2.0 Hz, 1H), 6.80 (d, J=8.3 Hz, 1H), 4.24 (t, J=6.8 Hz, 2H), 3.54 (t, J=6.1 Hz, 2H), 3.07 (br. s., 6H), 2.05 (quin, J=6.6 Hz, 2H). MS (ESI): m/z 289.56 [M+H]+. UPLC: tR=0.57 min (UPLC-SQD: analytical—2 min).

Sources & evidence

ORD record
ord-b66d9de302344e1abe687714cf3c2baf
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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