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 252923Notes

Reaction equation

HRID 252923 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-45746bc301a74c98a834e90e0df22a69
Source dataset
uspto-grants-2011_01
Patent number
US07872000B2

Reaction notes

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