Pyrazine, 2-(chloromethyl)- → 3-(3-Methylisoxazol-5-yl)-6-(pyrazin-2-yl)methyloxy-1,2,4-triazolo[3,4-a]phthalazine

HRID 382944Notes

Reaction equation

HRID 382944 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2=[N:12][N:13]=[C:14]([C:15]3[O:19][N:18]=[C:17]([CH3:20])[CH:16]=3)[N:4]2[N:3]=1.CC1C=C(C2N3N=C(OCC4C=CC=CN=4)C4C(C3=NN=2)=CC=CC=4)ON=1.Cl[CH2:49][C:50]1[CH:55]=[N:54][CH:53]=[CH:52][N:51]=1>>[CH3:20][C:17]1[CH:16]=[C:15]([C:14]2[N:4]3[N:3]=[C:2]([O:1][CH2:49][C:50]4[CH:55]=[N:54][CH:53]=[CH:52][N:51]=4)[C:11]4[C:6]([C:5]3=[N:12][N:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=4)[O:19][N:18]=1

Participants

4

Reactant 3

HCID 170169Pyrazine, 2-(chloromethyl)-HCID 183618903-(3-Methylisoxazol-5-yl)-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-a]phthalazineHCID 1784235156-Hydroxy-3-(3-methylisoxazol-5-yl)-1,2,4-triazolo[3,4-a]phthalazine

Product 1

HCID 183618583-(3-Methylisoxazol-5-yl)-6-(pyrazin-2-yl)methyloxy-1,2,4-triazolo[3,4-a]phthalazine

Procedure

The title-compound was prepared from 6-hydroxy-3-(3-methylisoxazol-5-yl)-1,2,4-triazolo[3,4-a]phthalazine (generated from the product of Example 120 part a using the conditions described for the preparation of Intermediate 2) and 2-chloromethylpyrazine (prepared as described in Example 15 part a) using the procedure described in Example part b. 1H NMR (360 MHz, CDCl3) δ 2.48 (3H, s, CH3), 5.83 (2H, s, CH2), 7.03 (1H, s, Ar—H), 7.87 (1H, m, Ar—H), 8.01 (1H, m, Ar—H), 8.32 (1H, d, J=7.8 Hz, Ar—H), 8.62-8.68 (2H, m, 2 of Ar—H), 8.72 (1H, d, J=7.8 Hz, Ar—H), 8.99 (1H, s, Ar—H); MS (ES+) m/e 360 [MH]+; Anal. Found C, 60.24; H, 3.44; N, 27.03. C18H13N7O2 requires C, 60.16; H, 3.63; N, 27.28%.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-6701eac9e6e648c088a22510cc118120
Source dataset
uspto-grants-2001_10
Patent number
US06310203B1

Reaction notes

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