Sodium Hydroxide → HCID 58203925, compound

HRID 1849474Notes

Reaction equation

HRID 1849474 reaction equation
[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([C:23](=O)[CH3:24])[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][C:6]([CH3:26])=[N:5]1)([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:33].[Na+].[OH-].[Na+]>CO>[CH:1]([N:4]1[C:8]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:15]4[CH:22]=[C:21]([CH:23]([NH2:33])[CH3:24])[CH:20]=[CH:19][C:16]=4[C:17]=3[N:18]=2)=[N:7][C:6]([CH3:26])=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58203696HCID 58203696, compound

Product 1

HCID 58203925HCID 58203925, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-ethanone (0.126 g, 0.000342 mol) in methanol (5.0 mL) was added ammonium acetate (0.140 g, 0.00182 mol) then sodium cyanoborohydride (0.172 g, 0.00274 mol). The reaction was stirred at 50° C. overnight. The mixture was basified with 1N NaOH and extracted 3 times with methylene chloride. The organic phases were combined, dried with Na2SO4 and concentrated to give 1-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-ethylamine. MS(ESI+) 370.2.

Workup

  1. extractionextracted 3 times with methylene chloride
  2. dry with materialdried with Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fcec4ea48191492e992f978dbd439068
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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