2-Amino-5-bromo-N,N-diethylbenzamide → 6-amino-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N,2-dimethyl benzamide

HRID 2279791Notes

Reaction equation

HRID 2279791 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)CC)=[O:5].N[C:25]1C(C(NC)=O)=C(C)C(Br)=CC=1.NC1C=CC(Br)=CC=1C(N(CC)CC)=O>>[NH2:1][C:2]1[C:3]([C:4]([NH:6][CH3:9])=[O:5])=[C:11]([CH3:25])[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

4

Reactant 3

HCID 509995132-Amino-5-bromo-N,N-diethylbenzamide2×HCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamideHCID 866977396-amino-3-bromo-2-methyl-N-methylbenzamide

Product 1

HCID 678188446-amino-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-N,2-dimethyl benzamide

Procedure

Prepared analogously to Compound 3C substituting 6-amino-3-bromo-2-methyl-N-methylbenzamide (Compound 29D) for 2-amino-5-bromo-N,N-diethylbenzamide (Compound 3D). MS (ESI): m/z=289.29 [M+H]+. UPLC: tR=2.33 min (ZQ3: polar—5 min).

Workup

  1. customtR=2.33 min (ZQ3: polar—5 min)

Sources & evidence

ORD record
ord-d2e38db14cec4cb7ae83b80baae07b90
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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