Water → HCID 86651541, compound

HRID 1809460Notes

Reaction equation

HRID 1809460 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:16](=[O:17])[C:15]2[N:18]3[C:8](=[C:9]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][NH:26][CH3:27])=[CH:21][CH:20]=4)[N:10]=[C:11]3[CH:12]=[CH:13][CH:14]=2)[CH2:7]1.O.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>>[F:38][C:37]([F:40])([F:39])[C:35]([O-:41])=[O:36].[CH3:27][NH2+:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:9]2[N:10]=[C:11]3[N:18]4[C:15]([C:16](=[O:17])[NH:6][CH2:7][C:8]=24)=[CH:14][CH:13]=[CH:12]3)=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 68634168HCID 68634168, compound

Product 1

HCID 86651541HCID 86651541, compound

Procedure

4-(2,4-dimethoxybenzyl)-2-{4-[(methylamino)methyl]phenyl}-3,4-dihydro-5H-1,4,8b-triazaacenaphthylen-5-one was dissolved in TFA:H2O:TIPS=8.0:1.5:0.5 (0.1 M) and heated to 120° C. for 30 min at microwave apparatus. The solvent was reduced in vacuo and the crude was purified by reverse phase HPLC (column: C18), using H2O (+0.1% TFA) and MeCN (+0.1% TFA) as eluents, the desired fractions were lyophilized to yield (15% over two steps) the title compound. 1H NMR (400 MHz, DMSO-d6, 300K) δ 8.76 (1H, bs), 8.68 (1H, s) 7.86 (2H, d, J=8.0 Hz), 7.68 (1H, d, J=9.0 Hz), 7.57 (2H, d, J=8.0 Hz), 7.37 (1H, d, J=7.0 Hz), 7.30 (1H, dd, J=9.0, 7.0 Hz), 5.28 (2H, s), 4.17 (2H, s), 2.60 (3H, s). MS (ES+) C17H16N4O requires: 292, found: 293 (M+H)+.

Workup

  1. customthe crude was purified by reverse phase HPLC (column: C18)

Sources & evidence

ORD record
ord-9ee298aebcf34cd387a92a8338d55060
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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