Nitrogen → HCID 21082000, compound

HRID 347011Notes

Reaction equation

HRID 347011 reaction equation
N#N.[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([C:28]4[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=4)([C:22]4[N:26]([CH3:27])[CH:25]=[N:24][N:23]=4)[NH2:21])[CH:18]=3)[N:13]3[N:35]=[N:36][N:37]=[C:12]3[N:11]=2)[CH:7]=[CH:8][CH:9]=1.[CH3:38][N:39](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:21][C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]1[N:35]=[N:36][N:37]=[C:12]1[N:11]=[C:10]2[C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=1)([C:22]1[N:26]([CH3:27])[CH:25]=[N:24][N:23]=1)[C:28]1[CH:33]=[CH:32][C:31]([C:38]#[N:39])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 6228DimethylformamideHCID 21082068HCID 21082068, compound

Product 1

HCID 21082000HCID 21082000, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

N2 was bubbled at room temperature in a solution of 5-(3-chlorophenyl)-α-(4-iodophenyl)-α-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine (0.0024 mol) in DMF (15 ml) for 1 hour. Zn(CN)2 (0.0036 mol) and Pd(PPh3)4 (0.0002 mol) were added. The mixture was stirred at 80° C. for 1 hour, cooled, poured out into ice water and extracted with EtOAc. The precipitate was filtered off (secondary product). The organic layer was washed twice with water then with saturated NaCl, separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2 to 80/20/2; 15–35 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.425 g (35%) of 4-[amino[5-(3-chlorophenyl)tetrazolo[1,5-a]quinazolin-7-yl](4-methyl-4H-1,2,4-triazol-3-yl)methyl]-benzonitrile which were crystallized from CH3CN. The precipitate was filtered off and dried, yielding 0.19 g (16%) of 4-[amino[5-(3-chlorophenyl)tetrazolo[1,5-a]quinazolin-7-yl](4methyl-4H-1,2,4-triazol-3-yl)methyl]-benzonitrile, mp. 194° C.

Workup

  1. temperaturecooled
  2. extractionextracted with EtOAc
  3. filtrationThe precipitate was filtered off (secondary product)
  4. washThe organic layer was washed twice with water
  5. customwith saturated NaCl, separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2 to 80/20/2; 15–35 μm)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-92207f2175b84a438a8b5d36acba5038
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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