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

HRID 2279796Notes

Reaction equation

HRID 2279796 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].NC1C([C:31](NC)=[O:32])=C(OC)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]([O:32][CH3:31])[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 866977426-Amino-3-bromo-2-methoxy-N-methylbenzamide

Product 1

HCID 678167876-amino-3-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methoxy-N-methyl benzamide

Procedure

Prepared analogously to Compound 3C substituting 6-amino-3-bromo-2-methoxy-N-methylbenzamide (Compound 30D) for 2-amino-5-bromo-N,N-diethylbenzamide (Compound 3D). MS (ESI): m/z=305.23 [M+H]+. HPLC: tR=2.48 min (ZQ3: polar—5 min).

Workup

  1. customHPLC: tR=2.48 min (ZQ3: polar—5 min)

Sources & evidence

ORD record
ord-ea70de8710864cfd87bc08d5271d4652
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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