HCID 12582745, compound → HCID 25106572, compound

HRID 452386Notes

Reaction equation

HRID 452386 reaction equation
[NH:1]([C:3]1[N:8]=[N:7][C:6]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:5]=2[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]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)[CH2:28][CH2:27]2)=[CH:22][CH:21]=1)#[N:16]>C(O)(C)C>[CH:32]1([N:29]2[CH2:30][CH2:31][N:26]([C:23]3[CH:22]=[CH:21][C:20]([NH:19][C:18]4[N:17]=[C:15]([NH2:16])[N:1]([C:3]5[N:8]=[N:7][C:6]6[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:5]=6[CH:4]=5)[N:2]=4)=[CH:25][CH:24]=3)[CH2:27][CH2:28]2)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 12582745HCID 12582745, compoundHCID 178512271HCID 178512271, compound

Product 1

HCID 25106572HCID 25106572, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[c]pyridazine (101 mg, 0.53 mmol) and (Z)-phenyl N′-cyano-N-(4-(4-cyclohexylpiperazin-1-yl)phenyl)carbamimidate (212 mg, 0.53 mmol) were suspended in isopropanol (3 mL) and subjected to microwave irradiation (150° C., 20 min). A portion of the crude product was purified by C-18 reversed phase hplc to give N3-(4-(4-cyclohexylpiperazin-1-yl)phenyl)-1-(5,6,7,8,9,10-hexahydrocycloocta[c]pyridazin-3-yl)-1H-1,2,4-triazole-3,5-diamine, compound #16, 17 mg. 1H NMR (CDCl3, 300 MHz) 8.41 (s, 1H), 7.55 (d, 2H), 6.92 (d, 2H), 3.38 (m, 3H), 3.15 (m, 6H), 2.96 (m, 1H), 2.80 (m, 2H), 2.11 (m, 2H), 1.67-1.90 (m, 7H), 1.05-1.45 (m, 10H) ppm; MS (ES) 502.28 (M+H).

Workup

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

Sources & evidence

ORD record
ord-a22005b8c6304b91a9c29e106ebb104a
Source dataset
uspto-grants-2013_07
Patent number
US08492373B2

Reaction notes

Loading…