Hydrochloric Acid → HCID 178420058, compound

HRID 378836Notes

Reaction equation

HRID 378836 reaction equation
[C:1]1([C:7]2[C:12]([O:13][CH2:14][C:15]3[N:16](COCC[Si](C)(C)C)[N:17]=[CH:18][N:19]=3)=[N:11][N:10]3[C:28]([C:31]4[CH:36]=[N:35][CH:34]=[CH:33][N:32]=4)=[N:29][N:30]=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:1]1([C:7]2[C:12]([O:13][CH2:14][C:15]3[N:19]=[CH:18][NH:17][N:16]=3)=[N:11][N:10]3[C:28]([C:31]4[CH:36]=[N:35][CH:34]=[CH:33][N:32]=4)=[N:29][N:30]=[C:9]3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 21696913HCID 21696913, compound

Product 1

HCID 178420058HCID 178420058, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

The product from Example 3 step b) (0.3 g) was suspended in ethanol (10 ml) with 2 N hydrochloric acid (21 ml) and heated at 65° C. for 5.5 h. Saturated sodium carbonate solution was added dropwise until a solid precipitated and this was collected by filtration and washed several times with water in the sinter funnel. The solid was recrystallised from methanol to give the required product (0.115 g, m.p. 255° C.). 1H NMR (360 MHz, DMSO) δ 5.64 (2H, s), 7.50 (3H, m), 7.62 (2H, m), 8.08 (1H, s), 8.16 (1H, s), 8.84 (1H, s), 8.90 (1H, s), 9.85 (1H, s); MS (ES+) m/e 372 [MH+]. Anal. Found C, 58.21; H, 3.53; N, 33.95. C18H13N9O requires C, 58.16; H, 3.26; N, 33.39%.

Workup

  1. customprecipitated
  2. filtrationthis was collected by filtration
  3. washwashed several times with water in the sinter funnel
  4. customThe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-f54723fefe1444b290d10e556022458f
Source dataset
uspto-grants-2001_10
Patent number
US06297235B1

Reaction notes

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