4-Chloro-7-(3-chloropropoxy)quinazoline → tert-butyl (4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetate

HRID 640007Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:6]=1.Cl[C:16]1[C:25]2[C:20](=[CH:21][C:22]([O:26][CH2:27][CH2:28][CH2:29][Cl:30])=[CH:23][CH:24]=2)[N:19]=[CH:18][N:17]=1>C(O)(C)C.C(OCC)C>[Cl:30][CH2:29][CH2:28][CH2:27][O:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([NH:1][C:2]3[CH:3]=[N:4][N:5]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:6]=3)=[N:17][CH:18]=[N:19]2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of tert-butyl (4-amino-1H-pyrazol-1-yl)acetate (0.305 g, 1.55 mmol) and 4-chloro-7-(3-chloropropoxy)quinazoline (0.398 g, 1.55 mmol) in isopropanol (8 ml) was heated at 90° C. for 5 minutes and then allowed to cool to room temperature. The mixture was diluted with diethyl ether and then filtered to give tert-butyl (4-{[7-(3-chloropropoxy)quinazolin-4-yl]amino}-1H-pyrazol-1-yl)acetate as the hydrochloride salt (0.674 g, 96% yield):

Workup

temperatureto cool to room temperature
filtrationfiltered

Sources & evidence

ORD record: ord-a3f194dd50304873ac6e65d3ca5fd52b
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

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