Pyrrolidine → 3-[2-Methyl-5-(2-pyrrolidin-1-ylpyrid-4-ylcarbonylamino)phenyl]-6-(4-methylpiperazin-1-yl)-3,4-dihydroquinazolin-4-one

HRID 2055095Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([CH3:35])=[C:15]([N:17]3[C:26](=[O:27])[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([N:28]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]5)[CH:24]=4)[N:19]=[CH:18]3)[CH:16]=2)=[O:9])[CH:5]=[CH:4][N:3]=1.[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>O>[CH3:35][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:7]=2)=[O:9])=[CH:16][C:15]=1[N:17]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([N:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)[CH:24]=2)[N:19]=[CH:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-[5-(2-chloropyrid-4-ylcarbonylamino)-2-methylphenyl]-6-(4-methylpiperazin-1-yl)-3,4-dihydroquinazolin-4-one (0.18 g) and pyrrolidine (2 ml) was stirred and heated to 100° C. for 16 hours. The mixture was cooled to ambient temperature and poured into water. The resultant solid was isolated, washed with water and dried under vacuum at 40° C. There was thus obtained the title compound (0.11 g); NMR Spectrum: (DMSOd6) 1.94-1.97 (m, 4H), 2.04 (s, 3H), 2.22 (s, 3H), 2.45-2.49 (m, 4H), 3.25-3.28 (m, 4H), 3.4-3.45 (m, 4H), 6.85 (s, 1H), 6.96 (d, 1H), 7.42 (d, 1H), 7.42 (d, 1H), 7.44 (s, 1H), 7.62 (s, 2H), 7.77-7.79 (m, 2H), 8.07 (s, 1H), 8.2 (s, 1H), 10.42 (s, 1H); Mass Spectrum: M+H+ 524.

Workup

temperatureThe mixture was cooled to ambient temperature
customThe resultant solid was isolated
washwashed with water
customdried under vacuum at 40° C

Sources & evidence

ORD record: ord-ea5416ad3ae6489aa783ccf7b10eb0f9
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07332483B2

Reaction notes

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