2-Hydrazino-5,6-dihydrobenzo[h]quinazoline → 1-(5,6-dihydrobenzo[h]quinazolin-2-yl)-N3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-1,2,4-triazole-3,5-diamine

HRID 1400094Notes

Reaction equation

[NH:1]([C:3]1[N:12]=[CH:11][C:10]2[CH2:9][CH2:8][C:7]3[CH:13]=[CH:14][CH:15]=[CH:16][C:6]=3[C:5]=2[N:4]=1)[NH2:2].[C:17](/[N:19]=[C:20](\OC1C=CC=CC=1)/[NH:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[CH:24][CH:23]=1)#[N:18]>C(O)(C)C>[N:4]1[C:5]2[C:6]3[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=3[CH2:8][CH2:9][C:10]=2[CH:11]=[N:12][C:3]=1[N:1]1[C:17]([NH2:18])=[N:19][C:20]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([N:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)=[CH:26][CH:27]=2)=[N:2]1

Participants

Conditions

Temperature: -20 °C

Procedure

2-Hydrazinyl-5,6-dihydrobenzo[h]quinazoline (40 mg, 0.19 mmol) and (Z)-phenyl N′-cyano-N-(4-(4-methylpiperazin-1-yl)phenyl)carbamimidate (67 mg, 0.20 mMol) were suspended in isopropanol and subjected to microwave irradiation (150° C., 20 min). A precipitate formed in the microwave vial. After further cooling at −20° C., the solid was filtered off, washed with cold isopropanol and dried under vacuum to give 1-(5,6-dihydrobenzo[h]quinazolin-2-yl)-N3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-1,2,4-triazole-3,5-diamine, compound #92, 32 mg; 1H NMR (DMSO-d6, 300 MHz) 8.76 (s, 1H), 8.65 (s, 1H), 8.16 (d, 1H), 7.65 (s, 2H), 7.46-7.53 (m, 4H), 7.37 (m, 1H), 6.84 (d, 2H), 2.90-3.05 (m, 8H), 2.48 (m, 4H), 2.22 (s, 3H) ppm; MS (ES) 454.17 (M+H).

Workup

customsubjected to microwave irradiation (150° C., 20 min)
customA precipitate formed in the microwave vial
filtrationthe solid was filtered off
washwashed with cold isopropanol
customdried under vacuum

Sources & evidence

ORD record: ord-212f5b132c154a81bd2c094c8c6ce771
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906922B2

Reaction notes

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