Water → N-Hydroxy 2-{6-[[2-(2-methylimidazol-1-yl)ethyl](naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamide

HRID 2079789Notes

Reaction equation

HRID 2079789 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH2:8][N:9]([S:27]([C:30]2[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=2)(=[O:29])=[O:28])[CH:10]2[CH:15]3[CH:11]2[CH2:12][N:13]([C:16]2[N:21]=[CH:20][C:19]([C:22]([O:24]CC)=O)=[CH:18][N:17]=2)[CH2:14]3)[CH:4]=[CH:5][N:6]=1.Cl.[NH2:41][OH:42].[O-]CC.[Na+].O>CCO>[OH:42][NH:41][C:22]([C:19]1[CH:20]=[N:21][C:16]([N:13]2[CH2:14][CH:15]3[CH:11]([CH:10]3[N:9]([CH2:8][CH2:7][N:3]3[CH:4]=[CH:5][N:6]=[C:2]3[CH3:1])[S:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)(=[O:28])=[O:29])[CH2:12]2)=[N:17][CH:18]=1)=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 66875590HCID 66875590, compound

Product 1

HCID 86642468N-Hydroxy 2-{6-[[2-(2-methylimidazol-1-yl)ethyl](naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxamideYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 2-{6-[[2-(2-methylimidazol-1-yl)ethyl](naphthalene-2-sulfonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxylate (0.211 g, 0.38 mmol) in EtOH (6 ml) in a sealed tube, was added hydroxylamine hydrochloride (0.460 g, 6.6 mmol) and sodium ethoxide (0.358 g, 5.3 mmol). The mixture was heated at 50° C. for 18 h, then water (20 ml) was added, and the product extracted with DCM (3×100 ml) and EtOAc (2×100 ml). The combined organic extracts were dried (MgSO4) and concentrated and the product purified by recrystallisation (MeOH) to give the title compound as a white solid (40 mg, 20%). LCMS Purity >98%, m/z 534 [M+H]+, 1H NMR (300 MHz, d6-DMSO) δ: 1.71 (1H, m), 1.82 (2H, m), 2.34 (3H, s), 3.43-3.55 (4H, m), 3.71 (2H, d, J=11.9 Hz), 4.14 (2H, t, J=6.5 Hz), 6.76 (1H, d, J=1.2 Hz), 7.08 (1H, d, J=1.2 Hz), 7.66-7.76 (2H, m), 7.88 (1H, dd, J=1.8, 10.5 Hz), 8.06 (1H, dd, J=2.0, 7.1 Hz), 8.18 (1H, d, J=8.7 Hz), 8.25 (1H, dd, J=2.0, 8.9 Hz), 8.57-8.62 (3H, m), 8.98 (1H, br s), 11.02 (1H, br s).

Workup

  1. extractionthe product extracted with DCM (3×100 ml) and EtOAc (2×100 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customthe product purified by recrystallisation (MeOH)

Sources & evidence

ORD record
ord-3c91a97a0cd64e1baf40c77416ce74ab
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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