5,6-Dihydro-3-hydrazinobenzo(H)cinnoline → 1-(5,6-dihydrobenzo[h]cinnolin-3-yl)-N3-(3-fluoro-4-(4-(pyrrolidin-1-yl)piperidin-1-yl)phenyl)-1H-1,2,4-triazole-3,5-diamine

HRID 1400097Notes

Reaction equation

HRID 1400097 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[CH2:9][CH2:10][C:11]=2[CH:12]=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][CH:31]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH2:30][CH2:29]2)=[C:24]([F:39])[CH:23]=1)#[N:18]>C(O)(C)C>[N:5]1[C:6]2[C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[CH2:9][CH2:10][C:11]=2[CH:12]=[C:3]([N:1]2[C:17]([NH2:18])=[N:19][C:20]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][CH:31]([N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[CH2:30][CH2:29]4)=[C:24]([F:39])[CH:23]=3)=[N:2]2)[N:4]=1

Participants

4

Reactant 2

HCID 323445,6-Dihydro-3-hydrazinobenzo(H)cinnolineHCID 178512270HCID 178512270, compound

Product 1

HCID 597745201-(5,6-dihydrobenzo[h]cinnolin-3-yl)-N3-(3-fluoro-4-(4-(pyrrolidin-1-yl)piperidin-1-yl)phenyl)-1H-1,2,4-triazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Hydrazinyl-5,6-dihydrobenzo[h]cinnoline (51 mg, 0.24 mMol) and (Z)-phenyl N′-cyano-N-(3-fluoro-4-(4-(pyrrolidin-1-yl)piperidin-1-yl)phenyl)carbamimidate (98 mg, 0.24 mMol) were suspended in isopropanol (3 mL) and subjected to microwave irradiation (150° C., 20 min). The crude product was purified by radial chromatography on silica gel, eluting with 95% dichloromethane and 5% 2M ammonia in methanol to give 1-(5,6-dihydrobenzo[h]cinnolin-3-yl)-N3-(3-fluoro-4-(4-(pyrrolidin-1-yl)piperidin-1-yl)phenyl)-1H-1,2,4-triazole-3,5-diamine, compound #170; 1H NMR (CDCl3/MeOD4, 300 MHz) 10.84 (s, 1H), 8.43 (d, 1H), 7.75 (s, 1H), 7.61 (d, 1H), 7.41 (m, 2H), 7.26 (m, 2H), 6.93 (t, 1H), 3.42 (m, 2H), 3.00 (m, 3H), 2.60-2.75 (m, 6H), 2.15 (m, 1H), 1.98 (m, 2H), 1.74-1.95 (m, 7H) ppm; MS (ES) 526.43 (M+H).

Workup

  1. customsubjected to microwave irradiation (150° C., 20 min)
  2. customThe crude product was purified by radial chromatography on silica gel
  3. washeluting with 95% dichloromethane and 5% 2M ammonia in methanol

Sources & evidence

ORD record
ord-0651b344e35d4bcd8fce3ce7b4c2285b
Source dataset
uspto-grants-2014_12
Patent number
US08906922B2

Reaction notes

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