Sodium Hydroxide → HCID 22000402, compound

HRID 1976135Notes

Reaction equation

HRID 1976135 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[S:14][C:15]3[CH2:22][CH2:21][O:20][C:19]4[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=4[C:16]=3[N:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH3:3].N1([CH:36]=[O:37])C2C=CC=CC=2N=N1.[OH-].[Na+]>C1COCC1>[N:17]1[C:16]2[C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[O:20][CH2:21][CH2:22][C:15]=2[S:14][C:13]=1[NH:12][CH:9]1[CH2:10][CH2:11][CH:6]([CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH:36]=[O:37])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 22000385HCID 22000385, compound

Product 1

HCID 22000402HCID 22000402, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N2-{4-[(propylamino)methyl]cyclohexyl)-4,5-dihydrobenzo[2,3]oxepino[4,5-d][1,3]thiazol-2-amine (0.254 g, 0.68 mmol) in anhydrous THF (4 ml) was added 1H-benzotriazole-1-carboxaldehyde (0.110 g, 0.75 mmol). The solution was stirred at room temperature for 1 hour and then poured into 2N NaOH (50 ml) and extracted with EtOAc (60 ml). The extract was separated and evaporated to yield 295 mg of a viscous oil. Chromatography on silica-gel eluting with 1:1 EtOAc/hexane yielded 56% (152 mg) of the product as a white solid: 1H-NMR (CDCl3) δ 0.90 (3H, m), 1.14 (4H, m), 1.58 (2H, m), 1.78 (2H, m), 2.23 (2H, m), 3.20 (8H, m), 4.32 (2H, t, J=4.9 Hz), 5.03 (1H, m), 6.99 (1H, m), 7.12 (2H, m), 8.01 (0.5H, s), 8.11 (0.5H, s), 8.22 (1H, d); m.p. 53-55° C.; 400 (ESMS, MH+).

Workup

  1. extractionextracted with EtOAc (60 ml)
  2. customThe extract was separated
  3. customevaporated

Sources & evidence

ORD record
ord-b29af9f5e9e44da488a93ba06686fcaf
Source dataset
uspto-grants-2001_05
Patent number
US06225330B1

Reaction notes

Loading…