3-Hydrazino-6,7-dihydro-5h-benzo[6,7]cyclohepta[1,2-c]pyridazine → 1-(6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3-yl)-N3-(5',5'-dimethyl-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2'-[1,3]dioxane]-3-yl)-1H-1,2,4-triazole-3,5-diamine

HRID 1919477Notes

Reaction equation

HRID 1919477 reaction equation
[C:1]([N:3]=[C:4]([O-])[NH:5][C:6]1[CH:7]=[C:8]2[CH2:24][CH2:23][C:15]3([O:20][CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][O:16]3)[CH2:14][CH2:13][CH2:12][C:9]2=[N:10][CH:11]=1)#[N:2].[N:26]1[C:31]2[C:32]3[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=3[CH2:34][CH2:35][CH2:36][C:30]=2[CH:29]=[C:28]([NH:41][NH2:42])[N:27]=1>C(O)(C)C>[N:26]1[C:31]2[C:32]3[CH:40]=[CH:39][CH:38]=[CH:37][C:33]=3[CH2:34][CH2:35][CH2:36][C:30]=2[CH:29]=[C:28]([N:41]2[C:1]([NH2:2])=[N:3][C:4]([NH:5][C:6]3[CH:7]=[C:8]4[CH2:24][CH2:23][C:15]5([O:20][CH2:19][C:18]([CH3:21])([CH3:22])[CH2:17][O:16]5)[CH2:14][CH2:13][CH2:12][C:9]4=[N:10][CH:11]=3)=[N:42]2)[N:27]=1

Participants

4

Reactant 2

HCID 592955463-Hydrazino-6,7-dihydro-5h-benzo[6,7]cyclohepta[1,2-c]pyridazineHCID 178428806HCID 178428806, compound

Product 1

HCID 671040171-(6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3-yl)-N3-(5',5'-dimethyl-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2'-[1,3]dioxane]-3-yl)-1H-1,2,4-triazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N′-cyano-N-(5′,5′-dimethyl-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2′-[1,3]dioxane]-3-yl)carbamimidate (120 mg, 0.286 mmol) and (6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3-yl)hydrazine (65 mg, 0.286 mmol) in isopropyl alcohol (2 mL) was heated in microwave at 150° C. for 20 min, filtered, and washed with isopropanol to give 1-(6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazin-3-yl)-N3-(5′,5′-dimethyl-6,8,9,10-tetrahydro-5H-spiro[cycloocta[b]pyridine-7,2′-[1,3]dioxane]-3-yl)-1H-1,2,4-triazole-3,5-diamine, compound #247 (55 mg, 35%); 1H NMR (DMSO-d6, 300 MHz) 9.22 (s, 1H), 8.72 (d, 1H), 7.94 (s, 1H), 7.88 (s, 2H), 7.13 (m, 1H), 7.62 (d, 1H), 7.44 (m, 2H), 7.36 (m, 1H), 3.42 (s, 4H), 2.82 (t, 2H), 2.71 (m, 2H), 2.25 (m, 2H), 1.97 (d, 2H), 1.69 (m, 2H), 1.52 (m, 2H), 1.02 (d, 4H), 0.88 (d, 6H) ppm; MS (ES) 553.28 (M+H).

Workup

  1. filtrationfiltered
  2. washwashed with isopropanol

Sources & evidence

ORD record
ord-984150c851b34a6e940a1952030aba9c
Source dataset
uspto-grants-2012_05
Patent number
US08168636B2

Reaction notes

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