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 252918Notes

Reaction equation

HRID 252918 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-125c797a3eb6464b8972518f59d002e2
Source dataset
uspto-grants-2011_01
Patent number
US07872000B2

Reaction notes

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