HCID 57509908, compound → HCID 57510224, compound

HRID 624214Notes

Reaction equation

HRID 624214 reaction equation
N1C=C[C:3](B(O)O)=N1.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])=[CH:12][CH:11]=1.BrC1C=C2C(=CC=1)CN(C(N[C:41]1[CH:46]=[CH:45][C:44]([C:47](=O)[NH:48][CH2:49][CH2:50][CH3:51])=[CH:43][CH:42]=1)=O)C2>>[CH2:47]([N:48]([CH3:3])[CH2:49]/[CH:50]=[CH:51]/[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])=[CH:12][CH:11]=1)[C:44]1[CH:43]=[CH:42][CH:41]=[CH:46][CH:45]=1

Participants

4

Reactant 3

HCID 57509908HCID 57509908, compoundHCID 68752575HCID 68752575, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 57510224HCID 57510224, compound

Procedure

The title compound was prepared as described in Example 280, substituting (E)-N-benzyl-N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-amine for 1H-pyrazol-3-ylboronic acid and N-(4-bromophenyl)isoindoline-2-carboxamide for 5-bromo-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (400 MHz, DMSO-d6, Temp=90° C.) δ ppm 8.12 (s, 1H), 7.52 (m, 2H), 7.37-7.18 (m, 11H), 6.48 (d, J=15.8 Hz, 1H), 6.18 (dt, J=15.8, 6.5 Hz, 1H), 4.77 (s, 4H), 3.53 (s, 2H), 3.15 (dd, J=6.5, 1.4 Hz, 2H), 2.18 (s, 3H); MS (ESI(+)) m/e 398 (M+H)+.

Sources & evidence

ORD record
ord-020687e561f6411c962e248b185c64ea
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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