Sodium Bicarbonate → HCID 57594575, compound

HRID 1714555Notes

Reaction equation

HRID 1714555 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:13][N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])=[CH:7][CH:6]=1)=O.[Br:33][C:34]1[C:35]([NH2:40])=[N:36][CH:37]=[CH:38][CH:39]=1.C(=O)(O)[O-].[Na+]>C(O)(C)C>[Br:33][C:34]1[C:35]2[N:36]([CH:2]=[C:3]([C:5]3[CH:6]=[CH:7][C:8]([CH2:11][C@H:12]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:13][N:14]4[C:15](=[O:24])[C:16]5[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=5)[C:22]4=[O:23])=[CH:9][CH:10]=3)[N:40]=2)[CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 8177002-Amino-3-bromopyridineHCID 575944941,1-Dimethylethyl {(1S)-2-[4-(bromoacetyl)phenyl]-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}carbamate

Product 1

HCID 57594575HCID 57594575, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1,1-dimethylethyl {(1S)-2-[4-(bromoacetyl)phenyl]-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}carbamate (6.9 mmol), 3-bromo-2-pyridinamine (8.4 mmol), and sodium bicarbonate (10.4 mmol) in isopropanol (70 mL) were stirred at 80° C. for 18 h. The reaction was then cooled to RT and a precipitate formed which was filtered, washed with cold hexanes (3×100 mL), and dried to afford the title compound as light gray solid (72%). ESMS [M+H]+: 576.2.

Workup

  1. customa precipitate formed which
  2. filtrationwas filtered
  3. washwashed with cold hexanes (3×100 mL)
  4. customdried

Sources & evidence

ORD record
ord-31f3f356cfee4264b1be1aaf5814f000
Source dataset
uspto-grants-2010_09
Patent number
US07795448B2

Reaction notes

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