Water → HCID 18361815, compound

HRID 1531775Notes

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: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.[H-].[Na+].I[CH:30]([CH3:32])[CH3:31].O>CN(C)C=O>[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][N:24]([CH:30]([CH3:32])[CH3:31])[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: 0 °C

Procedure

To a stirred solution of 3-(5-methylisoxazol-3-yl)-6-(1,2,4-triazol-3-yl)methyloxy-1,2,4-triazolo[3,4-a]phthalazine (100 mg, 0.29 mmol) in N,N-dimethylformamide (6 ml) at room temperature under nitrogen was added sodium hydride (17 mg, 0.41 mmol). The mixture was cooled to 0° C. and 2-iodopropane (0.04 ml, 0.36 mmol) added after 0.25 h. The mixture was left to stir at room temperature overnight, water was added and the precipitate filtered off. The crude product was flash chromatographed on silica gel, eluting with ethyl acetate→4% methanol/ethyl acetate, to give the title-product (25 mg, 22%), mp 179-181° C.; 1H NMR (360 MHz, CDCl3) δ 1.58 (6H, d, J=6.7 Hz, 2 of CH3), 2.59 (3H, s, CH3), 4.58 (1H, septet, J=6.7 Hz, CH), 5.72 (2H, s, CH2), 7.01 (1H, s, Ar—H), 7.78 (1H, t, J=7.2 Hz, Ar—H), 7.94 (1H, t, J=7.6 Hz, Ar—H), 8.13 (1H, s, Ar—H), 8.28 (1H, d, J=7.9 Hz, Ar—H), 8.80 (1H, d, J=7.4 Hz, Ar—H); MS (ES30) m/e 391 [MH]+; Anal. Found. C, 56.81; H, 4.68; N, 27.89; C19H18N8O2.0.7H2O requires C, 56.62; H, 4.85; N, 27.80%.

Workup

waitThe mixture was left
filtrationthe precipitate filtered off
customchromatographed on silica gel
washeluting with ethyl acetate→4% methanol/ethyl acetate

Sources & evidence

ORD record: ord-fd8c6e66c8c941e8b952118d099dae71
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200975B1

Reaction notes

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