Water → HCID 22457771, compound

HRID 1383850Notes

Reaction equation

HRID 1383850 reaction equation
[C:1]1([C:7]2[N:11]3[N:12]=[C:13]([O:22][CH2:23][C:24]4[NH:25][N:26]=[CH:27][N:28]=4)[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:15][C:10]3=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:32][C:33]#[N:34].O>CN(C=O)C>[C:1]1([C:7]2[N:11]3[N:12]=[C:13]([O:22][CH2:23][C:24]4[N:28]=[CH:27][N:26]([CH2:32][C:33]#[N:34])[N:25]=4)[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:15][C:10]3=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 17895490HCID 17895490, compound

Product 1

HCID 22457771HCID 22457771, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 72 Step c) (0.10 g) was suspended in DMF (5 ml). Sodium hydride (15 mg of a 60% dispersion in mineral oil) was added, and the mixture strrred at room temperature for 15 min. Chloroacetonitrile (41 μl) was added, and the mixture stirred as before for 2 days. Water (25 ml) was added, and the resultant precipitate filtered off and purified by flash chromatography (silica gel, 0 to 3% methanol in dichloromethane). The product was recrystallised from ethyl acetate/ethanol to yield colourless crystals (17 mg). 1H NMR (360 MHz, d6-DMSO) δ5.60 (2 H, s), 5.61 (2 H, s), 7.58 (6 H, m), 7.76 (2 H, m), 8.41 (1 H, s), 8.44 (2 H, m), 8.68 (1 H, s); MS (ES+) m/e 409 [MH+]. Anal. Found C, 64.62; H, 3.74; N, 26.82. C22H16N8O. 0.1 C4H8O2 requires C, 64.62; H, 4.06; N, 26.87%.

Workup

  1. filtrationthe resultant precipitate filtered off
  2. custompurified by flash chromatography (silica gel, 0 to 3% methanol in dichloromethane)
  3. customThe product was recrystallised from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-734fce3ef4504449ad0e9cd0a38a804c
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

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