Trifluoroacetic acid → HCID 136042751, compound

HRID 1921648Notes

Reaction equation

COC1C=CC(C[N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][C:20]4[N:24]5[N:25]=[C:26]([C:29]6[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=6)[CH:27]=[CH:28][C:23]5=[N:22][N:21]=4)[CH:15]=3)[N:10]=[CH:9]2)=CC=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[N:31]1[CH:32]=[CH:33][CH:34]=[C:29]([C:26]2[CH:27]=[CH:28][C:23]3[N:24]([C:20]([CH2:19][C:14]4[CH:15]=[C:16]5[C:11](=[CH:12][CH:13]=4)[N:10]=[CH:9][NH:8][C:17]5=[O:18])=[N:21][N:22]=3)[N:25]=2)[CH:30]=1

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 57654553HCID 57654553, compound

Product 1

HCID 136042751HCID 136042751, compoundYield 35%

Conditions

Temperature: 90 °C

Procedure

3-(4-Methoxy-benzyl)-6-(6-pyridin-3-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3H quinazolin-4-one (0.010 mg, 0.021 mmol) was treated with trifluoroacetic acid (1 mL) and anisole (0.1 mL) and heated to 90° C. for 18 hours. The compound was purified via reverse phase HPLC on a C18 column eluting with acetonitrile in water (0.1% TFA) to give 0.0026 g (35%) of 6-(6-pyridin-3-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-3H-quinazolin-4-one. 1H NMR (400 MHz, DMSO-d6) δ 9.32 (m, 1H), 8.79 (m, 1H), 8.53 (m, 2H), 8.20 (m, 1H), 8.10 (s, 1H), 8.03 (d, 1H, J=10.0 Hz), 7.89 (d, 1H, J=8.4 Hz), 7.66 (m, 2H), 4.80 (s, 2H). Mass spectrum (LCMS, ESI pos.): Calcd for C19H13N7O; found: 356.3, 357.3 (M+H).

Workup

customThe compound was purified via reverse phase HPLC on a C18 column
washeluting with acetonitrile in water (0.1% TFA)

Sources & evidence

ORD record: ord-60c60c11ed18474cb556c90278c93a91
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173654B2

Reaction notes

Loading…