HCID 57509908, compound → HCID 57509952, compound

HRID 624127Notes

Reaction equation

HRID 624127 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3](B(O)O)=[N:2]1.Br[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:19]2[CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)=[O:18])=[C:12]([F:28])[CH:11]=1.Br[C:30]1[CH:31]=C2C(=C[CH:38]=1)CN(C(NC1C=CC(C(=O)NCCC)=CC=1)=O)C2>>[F:28][C:12]1[CH:11]=[C:10]([C:4]2[CH:3]=[N:2][N:1]([CH2:38][CH2:30][CH3:31])[CH:5]=2)[CH:15]=[CH:14][C:13]=1[NH:16][C:17]([N:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1)=[O:18]

Participants

4

Reactant 3

HCID 57509908HCID 57509908, compoundHCID 68753313HCID 68753313, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 57509952HCID 57509952, compound

Procedure

The title compound was prepared as described in Example 280, substituting 1-propyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1H-pyrazol-3-ylboronic acid and N-(4-bromo-2-fluorophenyl)isoindoline-2-carboxamide for 5-bromo-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.19 (s, 1H), 8.03 (s, 1H), 7.89 (s, 1H), 7.57 (t, J=8.4 Hz, 1H), 7.46 (dd, J=12.1, 1.9 Hz, 1H), 7.24-7.39 (m, 5H), 4.76-4.78 (bs, 4H), 4.06 (t, J=6.9 Hz, 2H), 1.75-1.88 (m, 2H), 0.86 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 365 (M+H)+.

Sources & evidence

ORD record
ord-6b8d0f2448db4abbb1ee6180dae14e24
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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