HCID 21889488, compound → HCID 18361783, compound

HRID 382935Notes

Reaction equation

HRID 382935 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.[F:27][C:28]([F:35])([F:34])[CH2:29]S([O-])(=O)=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]([CH2:29][C:28]([F:35])([F:34])[F:27])[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

3

Reactant 2

HCID 21889488HCID 21889488, compoundHCID 178423514HCID 178423514, compound

Product 1

HCID 18361783HCID 18361783, compound

Procedure

The title-compound was prepared from 3-(5-methylisoxazol-3-yl)-6-(1,2,4-triazol-3-yl)methyloxy-1,2,4-triazolo[3,4-a]phthalazine and 2,2,2-trifluoroethylsulphonate following the procedure given for Example 47. The two regioisomers were separated by M.P.L.C. [Lobar Lichroprep Si60 (40-63 μm) (Art. 10402)], eluting with 2.5% methanol/dichloromethane, to give the title-product as the more polar isomer, 1H NMR (360 MHz, CDCl3) δ 8 2.58 (3H, s, CH3), 4.81 (2H, q, J=8.1 Hz, CH2), 5.75 (2H, s, CH2), 6.94 (1H, d, J=0.7 Hz, Ar—H), 7.80 (1H, t, J=7.2 Hz, Ar—H), 7.98 (1H, t, J=8.0 Hz, Ar—H), 8.26-8.28 (2H, m, Ar—H), 8.70 (1H, d, J=7.7 Hz, Ar—H); MS (ES+) m/e 431 [MH]+.

Workup

  1. customThe two regioisomers were separated by M.P.L.C
  2. wash[Lobar Lichroprep Si60 (40-63 μm) (Art. 10402)], eluting with 2.5% methanol/dichloromethane
  3. customto give the title-product as the more polar isomer, 1H NMR (360 MHz, CDCl3) δ 8 2.58 (3H, s, CH3), 4.81 (2H, q, J=8.1 Hz, CH2), 5.75 (2H, s, CH2), 6.94 (1H, d, J=0.7 Hz, Ar—H), 7.80 (1H, t, J=7.2 Hz, Ar—H), 7.98 (1H, t, J=8.0 Hz, Ar—H), 8.26-8.28 (2H, m, Ar—H), 8.70 (1H, d, J=7.7 Hz, Ar—H)

Sources & evidence

ORD record
ord-392d541d283e421d9b200f08eaeaf9f7
Source dataset
uspto-grants-2001_10
Patent number
US06310203B1

Reaction notes

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