Methyl N-(triethylammoniosulfonyl)carbamate → HCID 131724942, compound

HRID 2183514Notes

Reaction equation

HRID 2183514 reaction equation
CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.O[C:17]1([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][O:37][C:38]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[C:41]4=[N:48][N:49]=[C:50]([C:51]5[CH:55]=[C:54]([CH3:56])[O:53][N:52]=5)[N:40]4[N:39]=3)=[CH:32][N:31]=2)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1>ClCCCl>[CH3:56][C:54]1[O:53][N:52]=[C:51]([C:50]2[N:40]3[N:39]=[C:38]([O:37][CH2:36][C:33]4[CH:34]=[CH:35][C:30]([C:17]5[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]=5)=[N:31][CH:32]=4)[C:47]4[C:42]([C:41]3=[N:48][N:49]=2)=[CH:43][CH:44]=[CH:45][CH:46]=4)[CH:55]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 58298364HCID 58298364, compound

Product 1

HCID 131724942HCID 131724942, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Burgess reagent (262 mg, 1.1 mmol) was added to a stirred solution of 1,1-dimethylethyl 4-hydroxy-4-[5-({[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-α]phthalazin-6-yl]oxy}methyl)pyridin-2-yl]-1-piperidine carboxylate (307 mg, 0.55 mmol) in 1,2-dichloroethane (20 ml) at room temperature under N2 and the reaction heated at reflux for 90 min. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure while dry loading onto silica. The residue was purified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3 to yield the desired phthalazine (296 mg, 99%). 1H NMR (360 MHz, CDCl3) δ 8.86 (1H, s), 8.66 (1H, d, J=8.0 Hz), 8.20 (1H, d, J=8.0 Hz), 8.05-8.00 (1H, m), 7.95 (1H, t, J=8.0 Hz), 7.79 (1H, t, J=8.0 Hz), 7.43 (1H, d, J=8.1 Hz), 6.85 (1H, s), 6.66 (1H, m), 5.67 (2H, s), 4.17-4.11 (2H, m), 3.67-3.58 (2H, m), 2.68-2.60 (2H, m), 2.59 (3H, s), 1.49 (9H, s). m/z (ES+) 540 (M+H+).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 90 min
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customwhile dry loading onto silica
  5. customThe residue was purified by column chromatography on silica using 2% MeOH/CH2Cl2 containing 1% NH3

Sources & evidence

ORD record
ord-d2db6c7af1ba40fba19a4a0846025ab8
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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