Hydrochloric Acid → HCID 66747940, compound

HRID 1622859Notes

Reaction equation

HRID 1622859 reaction equation
Cl.N1C2=CC=CC3=CC=CC(=C23)N[B:3]1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22]([NH2:27])=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][CH:16]=1.C([O-])(O)=[O:29].[Na+].[OH-:33].[Na+]>C1COCC1.CCOC(C)=O>[NH2:27][C:22]1[C:21]([C:18]2[CH:19]=[CH:20][C:15]([B:3]([OH:29])[OH:33])=[CH:16][CH:17]=2)=[CH:26][CH:25]=[CH:24][N:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate2×HCID 66749464HCID 66749464, compound

Product 1

HCID 66747940HCID 66747940, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6N HCl aq. (1.1 mL) was added to a mixture of 3-(4-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)phenyl)pyridin-2-amine (396 mg) in THF (dry) (12 mL). The mixture was stirred at room temperature for 3 hr. The mixture was added with sat. NaHCO3 aq, EtOAc and 2N NaOH aq., and the separated aqueous phase was acidified by 6N HCl aq., then controlled pH ca. 8 by sat. NaHCO3 aq. The aqueous mixture was extracted with EtOAc, and the organic layer was separated, washed with brine dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound (52.4 mg) as a white solid.

Workup

  1. extractionwas extracted with EtOAc
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9fcbfdc08a974d32b527493327b3ecd8
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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