Sodium Bicarbonate → HCID 57594575, compound

HRID 730342Notes

Reaction equation

HRID 730342 reaction equation
CC([N:5]([C@H:9]([CH2:21][N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=O)[CH2:18]Br)=[CH:13][CH:12]=1)[C:6](=[O:8])[O-:7])(C)C.[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:18]=[C:17]([C:14]3[CH:15]=[CH:16][C:11]([CH2:10][C@H:9]([NH:5][C:6](=[O:8])[O:7][C:11]([CH3:16])([CH3:12])[CH3:10])[CH2:21][N:22]4[C:23](=[O:32])[C:24]5[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:30]4=[O:31])=[CH:12][CH:13]=3)[N:40]=2)[CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 8177002-Amino-3-bromopyridineHCID 86604763HCID 86604763, compound

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-ada4c48b7b724ec2b07ece6ae5fbfd30
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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