Ammonium Acetate → HCID 71256589, compound

HRID 1428977Notes

Reaction equation

HRID 1428977 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:27]=[CH:26][C:12]([CH2:13][O:14][C:15]3[CH:25]=[CH:24][C:18]4[N:19]=[C:20]([C:22]#[N:23])[S:21][C:17]=4[CH:16]=3)=[CH:11][CH:10]=2)[O:3]1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+]>CC(C)=O.O>[C:22]([C:20]1[S:21][C:17]2[CH:16]=[C:15]([O:14][CH2:13][C:12]3[CH:26]=[CH:27][C:9]([B:4]([OH:3])[OH:5])=[CH:10][CH:11]=3)[CH:25]=[CH:24][C:18]=2[N:19]=1)#[N:23]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 53492571HCID 53492571, compound

Product 1

HCID 71256589HCID 71256589, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 6-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)benzo[d]thiazole-2-carbonitrile (PBI 4472) (0.26 g, 0.66 mmol) in acetone (40 ml), a suspension of sodium periodate (0.43 g, 1.99 mmol), ammonium acetate (0.11 g, 1.33 mmol) in water (40 ml) was added at room temperature. The thick suspension was allowed to stir at room temperature for 18 hours. All solvent was evaporated, and the residue was dissolved in DMF. The suspension was centrifuged, and the clean solution was purified by prep-HPLC with acetonitrile/10% ammonium acetate to give the product as a white crystal (0.15 g, 72%). 1H NMR (300 MHz, DMSO, δ): 8.15 (d, J=9.0 Hz, 1H), 8.04 (s, 2H), 7.97 (d, J=3.0 Hz, 1H), 7.80 (d, J=9.0 Hz, 2H), 7.41 (m, 3H), 5.23 (s, 2H); MS (ESI) m/z 311.1.

Workup

  1. additionwas added at room temperature
  2. customAll solvent was evaporated
  3. dissolutionthe residue was dissolved in DMF
  4. customthe clean solution was purified by prep-HPLC with acetonitrile/10% ammonium acetate

Sources & evidence

ORD record
ord-1c8e535f8c594552846f938fe0c6a9b7
Source dataset
uspto-grants-2015_01
Patent number
US08937183B2

Reaction notes

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