HCID 57509908, compound → HCID 57510189, compound

HRID 624198Notes

Reaction equation

HRID 624198 reaction equation
N1C=CC(B(O)O)=N1.Br[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[CH2:15][N:14]([C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:36])[CH2:30][CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:24][CH:23]=1)=[O:20])[CH2:13]2.BrC1C=C2C(=CC=1)CN(C(NC1C=C[C:53]([C:56](=O)[NH:57][CH2:58][CH2:59][CH3:60])=CC=1)=O)C2>>[CH:31]1([CH2:30][C:29]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([NH:21][C:19]([N:14]3[CH2:13][C:12]4[C:16](=[CH:17][CH:18]=[C:10]([C:59]5[CH:58]=[N:57][CH:56]=[CH:53][CH:60]=5)[CH:11]=4)[CH2:15]3)=[O:20])=[CH:23][CH:24]=2)=[O:36])[CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

4

Reactant 3

HCID 57509908HCID 57509908, compoundHCID 57510173HCID 57510173, compoundHCID 178514837HCID 178514837, compound

Product 1

HCID 57510189HCID 57510189, compound

Procedure

The title compound was prepared as described in Example 280, substituting pyridin-3-ylboronic acid for 1H-pyrazol-3-ylboronic acid and 5-bromo-N-(4-(2-cyclopentylacetamido)phenyl)isoindoline-2-carboxamide for 5-bromo-N-(4-(propylcarbamoyl)phenyl)isoindoline-2-carboxamide. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.70 (bs, 1H), 8.93-8.89 (m, 1H), 8.58 (dd, J=4.7, 1.6 Hz, 1H), 8.33 (s, 1H), 8.13-8.05 (m, 1H), 7.72 (bs, 1H), 7.71-7.64 (m, 1H), 7.54-7.44 (m, 6H), 4.81 (bs, 4H), 2.31-2.18 (m, 3H), 1.82-1.68 (m, 2H), 1.68-1.43 (m, 4H), 1.26-1.11 (m, 2H); MS (ESI(+)) m/e 441 (M+H)+.

Sources & evidence

ORD record
ord-e65a9ce3935647cfa08dc9c3e5311c24
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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