2-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine → N3-(3-fluoro-4-(4-methyl-1,4-diazepan-1-yl)phenyl)-1-(5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidin-2-yl)-1H-1,2,4-triazole-3,5-diamine

HRID 2406133Notes

Reaction equation

HRID 2406133 reaction equation
[NH:1]([C:3]1[N:4]=[CH:5][C:6]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:7]=2[N:8]=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[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[CH2:28][CH2:27]2)=[C:22]([F:34])[CH:21]=1)#[N:16]>CN1CCCC1=O>[F:34][C:22]1[CH:21]=[C:20]([NH:19][C:18]2[N:17]=[C:15]([NH2:16])[N:1]([C:3]3[N:4]=[CH:5][C:6]4[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:7]=4[N:8]=3)[N:2]=2)[CH:25]=[CH:24][C:23]=1[N:26]1[CH2:32][CH2:31][CH2:30][N:29]([CH3:33])[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 552819292-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidineHCID 178480434HCID 178480434, compound

Product 1

HCID 25106400N3-(3-fluoro-4-(4-methyl-1,4-diazepan-1-yl)phenyl)-1-(5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidin-2-yl)-1H-1,2,4-triazole-3,5-diamine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Hydrazinyl-5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidine (58 mg, 0.30 mmol) and (Z)-phenyl N′-cyano-N-(3-fluoro-4-(4-methyl-1,4-diazepan-1-yl)phenyl)carbamimidate (111 mg, 0.30 mmol) were dissolved in anhydrous N-methylpyrrolidone (0.5 mL) and subjected to microwave irradiation (220° C., 10 min). The crude reaction mixture was directly purified by C-18 reversed phase chromatography, eluting with acetonitrile and water containing 0.05% formic acid to give N3-(3-fluoro-4-(4-methyl-1,4-diazepan-1-yl)phenyl)-1-(5,6,7,8,9,10-hexahydrocycloocta[d]pyrimidin-2-yl)-1H-1,2,4-triazole-3,5-diamine, compound #4, as a beige solid, 30 mg; 1H NMR (CDCl3/MeOD4, 300 MHz) 8.22 (s, 1H), 8.19 (s, 1H), 7.26 (d, 1H), 6.93 (d, 1H), 6.71 (t, 1H), 3.23 (m, 6H), 3.16 (m, 2H), 2.81 (m, 2H), 2.69 (s, 3H), 2.61 (m, 2H), 2.12 (m, 2H), 1.69 (m, 2H), 1.56 (m, 2H), 1.27 (m, 4H) ppm; MS (ES) 466.27 (M+H).

Workup

  1. customsubjected to microwave irradiation (220° C., 10 min)
  2. customThe crude reaction mixture
  3. customwas directly purified by C-18
  4. washeluting with acetonitrile and water containing 0.05% formic acid

Sources & evidence

ORD record
ord-894affd2a23946f289946e6ec6185c62
Source dataset
uspto-grants-2014_08
Patent number
US08809347B2

Reaction notes

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