HCID 57509908, compound → HCID 57509949, compound

HRID 624126Notes

Reaction equation

HRID 624126 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3](B(O)O)=[N:2]1.Cl[C:10]1[N: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])=[CH:12][CH:11]=1.Br[C:29]1[CH:30]=C2C(=C[CH:37]=1)CN(C(NC1C=CC(C(=O)NCCC)=CC=1)=O)C2>>[CH2:37]([N:1]1[CH:5]=[C:4]([C:10]2[N:15]=[CH:14][C:13]([NH:16][C:17]([N:19]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)=[O:18])=[CH:12][CH:11]=2)[CH:3]=[N:2]1)[CH2:29][CH3:30]

Participants

4

Reactant 3

HCID 57509908HCID 57509908, compoundHCID 86665074HCID 86665074, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 57509949HCID 57509949, 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-(6-chloropyridin-3-yl)isoindoline-2-carboxamide for 5-bromo-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.90-8.92 (bs, 1H), 8.84 (d, J=2.5 Hz, 1H), 8.39 (s, 1H), 8.25 (dd, J=8.8, 2.5 Hz, 1H), 8.08 (s, 1H), 7.87 (d, J=8.8 Hz, 1H), 7.31-7.41 (m, 4H), 4.79-4.83 (bs, 4H), 4.13 (t, J=6.9 Hz, 2H), 1.77-1.89 (m, 2H), 0.86 (t, J=7.3 Hz, 3H); MS (ESI(+)) m/e 348 (M+H)+.

Sources & evidence

ORD record
ord-a87544cca9124ecd900b2556e759ba5c
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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