3-Pyridinylboronic acid → (R)-4-(1-amino-1-oxo-3-(4-(pyridin-3-yl)phenyl)propan-2-ylamino)-5-fluoro-2-(3-methylisothiazol-5-ylamino)benzamide

HRID 2201138Notes

Reaction equation

HRID 2201138 reaction equation
[NH2:1][C:2](=[O:35])[C@H:3]([NH:17][C:18]1[C:26]([F:27])=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[C:20]([NH:28][C:29]2[S:33][N:32]=[C:31]([CH3:34])[CH:30]=2)[CH:19]=1)[CH2:4][C:5]1[CH:10]=[CH:9][C:8](C2C=CN=CC=2)=[CH:7][CH:6]=1.[N:36]1[CH:41]=[CH:40][CH:39]=[C:38](B(O)O)[CH:37]=1>>[NH2:1][C:2](=[O:35])[C@H:3]([NH:17][C:18]1[C:26]([F:27])=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[C:20]([NH:28][C:29]2[S:33][N:32]=[C:31]([CH3:34])[CH:30]=2)[CH:19]=1)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:38]2[CH:37]=[N:36][CH:41]=[CH:40][CH:39]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 69284981HCID 69284981, compound

Product 1

HCID 69284498(R)-4-(1-amino-1-oxo-3-(4-(pyridin-3-yl)phenyl)propan-2-ylamino)-5-fluoro-2-(3-methylisothiazol-5-ylamino)benzamide

Procedure

The titled compound (13 mg) was synthesized analogously by procedures described in the Example for (R)-4-(1-amino-1-oxo-3-(4-(pyridin-4-yl)phenyl)propan-2-ylamino)-5-fluoro-2-(3-methylisothiazol-5-ylamino)benzamide, using pyridine-3-boronic acid in place of pyridine-4-boronic acid. MS 491.5 (M+H); UV 205.2, 244.2, 299.4 nm.

Sources & evidence

ORD record
ord-d5c0a59533b5497ba7956c506421391a
Source dataset
uspto-grants-2016_06
Patent number
US09359375B2

Reaction notes

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