Diisopropylethylamine → 5-fluoro-N-[1-(3-fluorobenzyl)-1H-indazol-5-yl]quinazolin-4-amine

HRID 1162239Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[CH:4][N:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:28]=[CH:29][CH:30]=1)[CH2:17][N:18]1[C:26]2[C:21](=[CH:22][C:23]([NH2:27])=[CH:24][CH:25]=2)[CH:20]=[N:19]1.C(N(C(C)C)CC)(C)C>C(O)(C)C>[F:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([NH:27][C:23]1[CH:22]=[C:21]3[C:26](=[CH:25][CH:24]=1)[N:18]([CH2:17][C:16]1[CH:28]=[CH:29][CH:30]=[C:14]([F:13])[CH:15]=1)[N:19]=[CH:20]3)=[N:3][CH:4]=[N:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-chloro-5-fluoroquinazoline (1.82 g, 10 mmol), 1-(3-fluorobenzyl)-1H-indazol-5-amine (2.41 g, 10 mmol, obtained as described in WO 98/02438) and diisopropylethylamine (1.74 ml, 10 mmol) in isopropanol (20 ml) was heated at 80° C. for 45 minutes. On cooling to ambient temperature, the product was filtered off and washed with isopropanol and ether. The precipitated solid was dried under high vacuum to give 5-fluoro-N-[1-(3-fluorobenzyl)-1H-indazol-5-yl]quinazolin-4-amine (3.2 g, 83%); NMR Spectrum (CDCl3) 5.61 (s, 2H), 6.88 (d, 1H), 6.98 (m, 2H), 7.25 (m, 2H), 7.37 (d, 1H), 7.53 (dd, 1H), 7.73 (m, 2H), 8.09 (s, 1H), 8.19 (s, 1H), 8.49 (d, 1H), 8.69 (s, 1H); Mass spectrum MH+ 388.

Workup

temperatureOn cooling to ambient temperature
filtrationthe product was filtered off
washwashed with isopropanol and ether
customThe precipitated solid was dried under high vacuum

Sources & evidence

ORD record: ord-5ddfa3122ea74a88a200397064e9190b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820683B2

Reaction notes

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