Sodium Carbonate → HCID 54426403, compound

HRID 1383844Notes

Reaction equation

[C:1]1([C:7]2[N:11]3[N:12]=[C:13]([O:22][CH2:23][C:24]4[N:28](COCC[Si](C)(C)C)[N:27]=[N:26][CH: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.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.Cl>[C:1]1([C:7]2[N:11]3[N:12]=[C:13]([O:22][CH2:23][C:24]4[CH:25]=[N:26][NH: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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of the product from Step c (0.7025 g, 1.41 mmol) in ethanol (12 ml) and 2 M aqueous HCl (25 ml) was stirred at 60° C. for 5.5 h. The mixture was then neutralised by adding dropwise saturated aqueous Na2CO3. The resulting precipitate was collected by filtration, washed with water, then hexane, and dried under vacuum at 60° C. This was purified by recrystallisation (MeOH—CH2Cl2), then flash chromatography (silica gel, 3-5% MeOH/CH2Cl2) to afford 0.2044 g (39%) of the title compound as a white solid: mp 208-220° C.; 1H NMR (360 MHz, d6-DMSO) δ5.66 (2 H, s), 7.48-7.49 (3 H, m), 7.58-7.72 (5 H, m), 7.94 (1 H, br s), 8.40 (1 H, s), 8.47 (2 H, d, J=7.2 Hz), 15.10 (1 H, br s); MS (ES+) m/e 370 [MH]+; Anal. Found C, 65.07; H, 4.05; N, 26.01. C20H15N7O.0.1 H2O requires C, 64.72; H, 4.13; N, 26.41%.

Workup

filtrationThe resulting precipitate was collected by filtration
washwashed with water
dry with materialhexane, and dried under vacuum at 60° C
customThis was purified by recrystallisation (MeOH—CH2Cl2)

Sources & evidence

ORD record: ord-9b85e3bcfee046af8e3cddd943c3dfca
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255305B1

Reaction notes

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