Sodium Hydroxide → HCID 59367693, compound

HRID 2079782Notes

Reaction equation

HRID 2079782 reaction equation
[OH-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([NH:16][CH:17]1[CH:22]2[CH:18]1[CH2:19][N:20]([C:23]1[N:28]=[CH:27][C:26]([C:29]([O:31]CC)=[O:30])=[CH:25][N:24]=1)[CH2:21]2)(=[O:15])=[O:14]>C1COCC1.CO>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([NH:16][CH:17]1[CH:18]2[CH:22]1[CH2:21][N:20]([C:23]1[N:28]=[CH:27][C:26]([C:29]([OH:31])=[O:30])=[CH:25][N:24]=1)[CH2:19]2)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59367563HCID 59367563, compound

Product 1

HCID 59367693HCID 59367693, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1M NaOH (500 ml) was added to a solution of ethyl 2-{6-[(2-napthylsulphonyl)amino]-3-azabicyclo[3.1.0]hex-3-yl}pyrimidine-5-carboxylate (25.40 g, 58.00 mmol) in THF (500 ml) and MeOH (100 ml) at r.t. The reaction mixture was stirred for 18 h. The organic solvents were removed in vacuo and the resultant aqueous solution was acidified to pH˜5 with 1M aq. HCl. A heavy white precipitate was formed which was isolated by filtration, washed with H2O and dried by azeotroping with toluene, giving the product as a white solid (22.19 g, 93%). LCMS purity 100%, m/z 411 [M+H]+, 1H NMR (400 MHz, d6-DMSO) δ: 1.97 (2H, s), 2.05 (1H, s), 3.64-3.67 (2H, m), 3.82-3.89 (2H, m), 7.84-7.88 (2H, m), 8.01 (1H, m), 8.21 (1H, d), 8.31-8.36 (3H, m), 8.66 (1H, s), 8.83 (2H, s).

Workup

  1. customThe organic solvents were removed in vacuo
  2. customA heavy white precipitate was formed which
  3. customwas isolated by filtration
  4. washwashed with H2O
  5. customdried
  6. customby azeotroping with toluene

Sources & evidence

ORD record
ord-f5128ab0955146c795949fe924a21e22
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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