2-Amino-5-bromo-N,N-diethylbenzamide → 7-amino-5-fluoro-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-2,3-dihydro-1H-isoindol-1-one

HRID 2279801Notes

Reaction equation

HRID 2279801 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=C([F:37])C(Br)=C2C=1C(=O)N(C)C2.NC1C=CC(Br)=CC=1C(N(CC)CC)=O>>[NH2:1][C:2]1[CH:14]=[C:13]([F:37])[C:12]([C:15]2[CH:16]=[N:17][N:18]([CH2:20][CH2:21][CH2:22][OH:23])[CH:19]=2)=[C:11]2[C:3]=1[C:4](=[O:5])[N:6]([CH3:7])[CH2:9]2

Participants

4

Reactant 3

HCID 509995132-Amino-5-bromo-N,N-diethylbenzamide2×HCID 678138277-amino-4-bromo-5-fluoro-2-methyl-2,3-dihydro-1H-isoindol-1-oneHCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 678115207-amino-5-fluoro-4-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]-2-methyl-2,3-dihydro-1H-isoindol-1-one

Procedure

Prepared analogously to Compound 3C substituting 7-amino-4-bromo-5-fluoro-2-methyl-2,3-dihydro-1H-isoindol-1-one (Compound 31D) for 2-amino-5-bromo-N,N-diethylbenzamide (Compound 3D). 1H NMR (CDCl3, 400 MHz): δ 7.75 (d, J=4.5 Hz, 2H), 6.41 (d, J=13.1 Hz, 1H), 4.46 (t, J=6.1 Hz, 2H), 4.39 (s, 2H), 3.70 (t, J=5.6 Hz, 2H), 3.17 (s, 3H), 2.20-2.09 (m, 3H). MS (ESI): m/z=305.14 [M+H]+. UPLC: tR=0.95 min (UPLC-TOF: polar—3 min).

Workup

  1. customtR=0.95 min (UPLC-TOF: polar—3 min)

Sources & evidence

ORD record
ord-67b75ec7c6eb4356a43db8564c15da3d
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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