Hydrochloric Acid → HCID 178423514, compound

HRID 382931Notes

Reaction equation

[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:11]3[N:12]=[C:13]([O:20][CH2:21][C:22]4[N:23](COCC[Si](C)(C)C)[N:24]=[CH:25][N:26]=4)[C:14]4[C:19]([C:10]3=[N:9][N:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:3]=1.Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[N:11]3[N:12]=[C:13]([O:20][CH2:21][C:22]4[N:26]=[CH:25][NH:24][N:23]=4)[C:14]4[C:19]([C:10]3=[N:9][N:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-(5-methylisoxazol-3-yl)-6-[2-{[2-(trimethylsilyl)ethoxy]methyl}-1,2,4-triazolyl]methyloxy-1,2,4-triazolo-[3,4-a]phthalazine (1.20 g, 2.5 mmol) in ethanol (20 ml) was added 2N hydrochloric acid (40 ml) at room temperature. The mixture was heated at 60° C. for 5 h, saturated potassium carbonate solution wad added and the solvent evaporated in vacuo. The solid was triturated with ethanol, filtered and the filtrate evaporated in vacuo. The residue was flash chromatographed on silica gel, eluting with 4% methanol/dichloromethane, to give the title-product (140 mg, 16%), mp 260-262° C.; 1H NMR (360 MHz, d6-DMSO) δ 2.56 (3H, s, me), 5.75 (2H, s, CH2), 7.24 (1H, s, Ar—H), 8.00 (1H, t, J=8.1 Hz, Ar—H), 8.14 (1H, t, J=7.7 Hz, Ar—H), 8.26 (1H, d, J=8.0 Hz, Ar—H), 8.60 (1H, br s, NH), 8.65 (1H, d, J=7.4 Hz, Ar—H); MS (ES+) m/e 349 [MH]+.

Workup

customthe solvent evaporated in vacuo
customThe solid was triturated with ethanol
filtrationfiltered
customthe filtrate evaporated in vacuo
customchromatographed on silica gel
washeluting with 4% methanol/dichloromethane

Sources & evidence

ORD record: ord-9393e18b619c4ffa98455c7c0376ebc1
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310203B1

Reaction notes

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