Lithium Hexamethyldisilazide → 3-(5-Fluoromethylisoxazol-3-yl)-6-(1-methyl-1,2,4-triazol-5-yl)methyloxy-1,2,4-triazolo[3,4-a]phthalazine

HRID 382933Notes

Reaction equation

HRID 382933 reaction equation
[F:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:12]3[N:13]=[C:14]([O:21][CH2:22][C:23]4C=CC=[CH:25][N:24]=4)[C:15]4[C:20]([C:11]3=[N:10][N:9]=2)=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:4]=1.C[N:30]1[C:34](CO)=[N:33]C=N1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[F:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[N:12]3[N:13]=[C:14]([O:21][CH2:22][C:23]4[N:24]([CH3:25])[N:33]=[CH:34][N:30]=4)[C:15]4[C:20]([C:11]3=[N:10][N:9]=2)=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH:4]=1

Participants

4

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 183618303-(5-Fluoromethylisoxazol-3-yl)-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-a]phthalazine

Product 1

HCID 183617593-(5-Fluoromethylisoxazol-3-yl)-6-(1-methyl-1,2,4-triazol-5-yl)methyloxy-1,2,4-triazolo[3,4-a]phthalazine

Procedure

The title-compound was prepared from the product of Example 66 part c (150 mg, 0.5 mmol) and 2-methyl-1,2,4-triazole-3-methanol (61 mg, 0.53 mmol) (prepared using the conditions of Itoh and Okongi, EP-A-421210) using the procedure given in Example 1 using lithium bis(trimethylsilyl)amide (0.59 ml, 1.0M in tetrahydrofuran) as the base (80 mg, 43%), mp 250-252° C.; 1H NMR (360 MHz, d6-DMSO) δ 4.01 (3H, s, CH3), 5.76 (2H, d, J=47 Hz, CH2), 5.83 (2H, s, CH2), 7.70 (1H, d, J=Hz, Ar—H), 7.96 (1H, m, Ar—H), 8.02 (1H, s, Ar—H), 8.13 (1H, m, Ar—H), 8.25 (1H, d, J=7.8 Hz, Ar—H), 8.59 (1H, d, J=7.9 Hz, Ar—H);M1S (ES+) m/e 381 [MH]+; Anal. Found. C, 52.31; H, 3.36; N, 28.64. C17H13N8O2F.0.15CH2Cl2 requires C, 52.40; H, 3.41; N, 28.51%.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-dc2f5d94af704705a42477d87feb6f49
Source dataset
uspto-grants-2001_10
Patent number
US06310203B1

Reaction notes

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