2-Hydrazinyl-5,6,7,8,9,10-hexahydrocyclooct[b]pyridine → 1-(5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl)-N3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-1,2,4-triazole-3,5-diamine

HRID 452389Notes

Reaction equation

HRID 452389 reaction equation
[NH:1]([C:3]1[N:8]=[C:7]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:6]2=[CH:5][CH:4]=1)[NH2:2].[C:15](/[N:17]=[C:18](\OC1C=CC=CC=1)/[NH:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1)#[N:16]>C(O)(C)C>[N:8]1[C:3]([N:1]2[C:15]([NH2:16])=[N:17][C:18]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]4)=[CH:24][CH:25]=3)=[N:2]2)=[CH:4][CH:5]=[C:6]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:7]=12

Participants

4

Reactant 2

HCID 552819282-Hydrazinyl-5,6,7,8,9,10-hexahydrocyclooct[b]pyridineHCID 178480746HCID 178480746, compound

Product 1

HCID 251066631-(5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl)-N3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-1,2,4-triazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine (81 mg, 0.42 mmol) and (Z)-phenyl N′-cyano-N-(4-(4-methylpiperazin-1-yl)phenyl)carbamimidate (142 mg, 0.42 mmol) were suspended in isopropanol and subjected to microwave irradiation (150° C., 20 min). The crude product was purified by C-18 reversed phase HPLC to give 1-(5,6,7,8,9,10-hexahydrocycloocta[b]pyridin-2-yl)-N3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-1,2,4-triazole-3,5-diamine, compound #23, as a white solid, 92 mg; 1H NMR (DMSO-d6, 300 MHz) 8.69 (s, 1H), 8.13 (s, 1H), 7.65 (d, 1H), 7.55 (s, 1H), 7.44 (d, 2H), 7.41 (d, 1H), 6.84 (d, 2H), 3.01 (m, 4H), 2.90 (m, 2H), 2.75 (m, 2H), 2.50 (m, 4H), 2.25 (s, 3H), 1.71 (m, 2H), 1.63 (m, 2H), 1.33 (m, 4H) ppm; MS (ES) 433.17 (M+H).

Workup

  1. customsubjected to microwave irradiation (150° C., 20 min)
  2. customThe crude product was purified by C-18

Sources & evidence

ORD record
ord-7563fd9d54904c2087f407500979fc2e
Source dataset
uspto-grants-2013_07
Patent number
US08492373B2

Reaction notes

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