Hydrochloric Acid → 6-[2-(1H-pyrazol-4-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]methylquinoline

HRID 1257893Notes

Reaction equation

C(OC([N:6]1[CH:10]=[C:9]([C:11]2[N:16]=[N:15][C:14]([NH2:17])=[N:13][CH:12]=2)[CH:8]=[N:7]1)C)C.Cl[CH:19]([CH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[CH:26]2)[CH:20]=O.Cl>C(O)(C)C>[NH:7]1[CH:8]=[C:9]([C:11]2[CH:12]=[N:13][C:14]3[N:15]([C:19]([CH2:22][C:23]4[CH:24]=[C:25]5[C:30](=[CH:31][CH:32]=4)[N:29]=[CH:28][CH:27]=[CH:26]5)=[CH:20][N:17]=3)[N:16]=2)[CH:10]=[N:6]1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-[1-(1-ethoxyethyl)-1H-pyrazol-4-yl]-1,2,4-triazin-3-amine (390.0 mg, 1.665 mmol) and 2-chloro-3-quinolin-6-ylpropanal (480 mg, 2.2 mmol) in isopropyl alcohol (20 mL) was heated at 110° C. for 2 days. After cooling to RT, 0.2 mL of concentrated HCl was added and stirred until completely deprotected. The solid formed was collected by filtration to give the desired product (0.35 g, 64%). LCMS: (M+H)=328.3.

Workup

temperatureAfter cooling to RT
customThe solid formed
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-448cb29d1fbb49b2bc6200d4a15dd7ae
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461330B2

Reaction notes

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