Trifluoroacetic acid → HCID 131724943, compound

HRID 2183515Notes

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[CH:23]=[CH:24][C:25]([C:28]5[CH2:29][CH2:30][N:31](C(OC(C)(C)C)=O)[CH2:32][CH:33]=5)=[N:26][CH:27]=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.FC(F)(F)C(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[CH:23]=[CH:24][C:25]([C:28]5[CH2:29][CH2:30][NH:31][CH2:32][CH:33]=5)=[N:26][CH:27]=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

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 131724942HCID 131724942, compound

Product 1

HCID 131724943HCID 131724943, compoundYield 51.3%

Procedure

The reaction was carried out according to Example 12 step 3 using 1,1-dimethylethyl 5-({[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-α]phthalazin-6-yl]oxy}methyl)-3′6′-dihydro-2,4′-bipyridine-1′(2′H)-carboxylate (296 mg, 0.55 mmol) and trifluoroacetic acid (5 ml). The crude residue was purified by column chromatography on silica using 7% MeOH/CH2Cl2 containing 1% NH3 to yield the desired phthalazine (124 mg, 51%). 1H NMR (360 MHz, CDCl3) δ 8.81 (1H, s), 8.68 (1H, d, J=7.6 Hz), 8.21 (1H, d, J=8.0 Hz), 8.05-7.90 (2H, m), 7.80 (1H, t, J=8.0 Hz), 7.43 (1H, t, J=8.1 Hz), 6.85 (1H, s), 6.75 (1H, broad s), 5.68 (2H, s), 3.60 (2H, q, J=2.9 Hz), 3.12 (2H, t, J=5.7 Hz), 2.67-2.55 (5H, m). m/z (ES+) 440 (M+H+).

Workup

customThe crude residue was purified by column chromatography on silica using 7% MeOH/CH2Cl2 containing 1% NH3

Sources & evidence

ORD record: ord-44f9ddfbc217484cbd6423fccce230b7
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900209B2

Reaction notes

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