2-Amino-5-bromopyridine → N-(5-Bromo-pyridin-2-yl)-3-[7-fluoro-2-(4-fluoro-benzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionamide

HRID 2402301Notes

Reaction equation

HRID 2402301 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([CH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:24]=[CH:23][C:19](C(O)=O)=[CH:18][N:17]=1)=[O:14])[N:8]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[C:7]2=[O:33].[Br:34]C1C=CC(N)=NC=1>>[Br:34][C:19]1[CH:23]=[CH:24][C:16]([NH:15][C:13](=[O:14])[CH2:12][CH2:11][CH:9]2[C:10]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[F:1])[C:7](=[O:33])[N:8]2[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[N:17][CH:18]=1

Participants

3

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 160587176-{3-[7-Fluoro-2-(4-fluorobenzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionylamino}-nicotinic acid

Product 1

HCID 16663092N-(5-Bromo-pyridin-2-yl)-3-[7-fluoro-2-(4-fluoro-benzyl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]-propionamide

Procedure

The product from Example 11, Part D (150 mg, 0.45 mmol) and 5-bromopyridin-2-ylamine (78 mg, 0.45 mmol) were converted to the title compound in a manner analogous to the method described in Example 27 (151 mg, 69%). 1H NMR (300 MHz, DMSO) δ 8.18 (d, J=2 Hz, 1H), 8.05 (m, 2H), 7.76 (dd, J=9 Hz, 3 Hz, 1H), 7.66 (d, J=7 Hz, 1H), 7.44 (m, 1H), 7.30 (m, 2H), 7.18 (t, J=9, 1H), 7.01 (t, J=7 Hz, 2H), 5.26 (d, J=15 Hz, 1H), 4.69 (m, 1H), 4.23 (d, J=15 Hz, 1H), 2.54 (m, 2H), 1.95 (m, 2H). MS: m/z (MH+) 486 (MH+ 2) 488.

Sources & evidence

ORD record
ord-6c91540918a0478b8263dc75be242739
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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