Sodium Hydroxide → HCID 68801647, compound

HRID 711693Notes

Reaction equation

HRID 711693 reaction equation
[S:1]([NH2:5])([NH2:4])(=[O:3])=[O:2].N[C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH:16]([CH3:18])[CH3:17])[C:8]=1[C:9]#[N:10].[OH-].[Na+]>CCO>[CH:16]([NH:15][C:11]1[C:8]2[C:9]([NH2:10])=[N:5][S:1](=[O:3])(=[O:2])[NH:4][C:7]=2[CH:14]=[CH:13][CH:12]=1)([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66747382HCID 66747382, compound

Product 1

HCID 68801647HCID 68801647, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-amino-6-(isopropylamino)benzonitrile sulfamide (Example 90a) (0.14 g, 0.54 mmol) and NaOH (2 N, 0.54 mL) in EtOH (3 mL) was stirred at 90° C. under nitrogen for 0.5 hour. The reaction mixture was cooled to room temperature, and concentrated under vacuum. H2O (1 mL) was added and the reaction mixture was neutralized to pH˜3 with 10% AcOH. The resultant precipitate was extracted with EtOAc, and after evaporation of solvents the residue was purified by preparative thin layer chromatography using a DCM/EtOAc (4:1) solution as eluant, to give N5-isopropyl-1H-benzo[c][1,2,6]thiadiazine-4,5-diamine-2,2-dioxide (0.02 g). 1H NMR (400 MHz, DMSO-d6) δ 1.11 (d, J=6.4 Hz, 6H), 1.84 (bs, 1H), 5.24 (bs, NH), 6.22-6.19 (m, 2H, NH), 7.09 (t, J=8.0 Hz, 1H), 7.48 (bs, 2H). MS 255 (MH+).

Workup

  1. concentrationconcentrated under vacuum
  2. additionH2O (1 mL) was added
  3. extractionThe resultant precipitate was extracted with EtOAc
  4. customafter evaporation of solvents the residue
  5. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-b508b15c65eb4ae39e71c09e7a305b94
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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