Pyridine → HCID 58032635, compound

HRID 1046895Notes

Reaction equation

HRID 1046895 reaction equation
[C:1]([C:4]1[CH:9]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:8]2[N:18]=[N:19][N:20]=[C:7]2[NH:6][C:5]=1[CH3:21])(=[O:3])[CH3:2].[F:22][C:23]([F:34])([F:33])[C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[C:1]([C:4]1[CH:9]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:8]2[N:18]=[N:19][N:20]=[C:7]2[N:6]([C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([C:23]([F:34])([F:33])[F:22])[CH:29]=2)[C:5]=1[CH3:21])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 8471Triethylamine2×HCID 27343883-(Trifluoromethyl)phenylboronic acid2×HCID 136133143HCID 136133143, compound

Product 1

HCID 58032635HCID 58032635, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Under an atmosphere of argon protective gas, (rac)-4-(6-acetyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile (50 mg, 178 μmol) was stirred in abs. dichloromethane (3 ml) with molecular sieve (0.5 g, 4 Å) for 1 h. 3-(Trifluoromethyl)phenylboronic acid (101.6 mg, 535 μmol, 3 eq.), anhydrous copper(II) acetate (97.2 mg, 535 μmol, 3 eq.), abs. pyridine (115 μl, 1.43 mmol, 8 eq.) and triethylamine (54.2 mg, 535 μmol, 3 eq.) were then added, and the mixture was stirred at RT for 12 h. More molecular sieve (0.5 g, 4 Å), 3-(trifluoromethyl)phenylboronic acid (33 mg, 178 μmol, 1 eq.), anhydrous copper(II) acetate (32 mg, 178 μmol, 1 eq.), triethylamine (18.1 mg, 178 μmol, 1 eq.) and abs. pyridine (57.5 μl, 715 μmol, 4 eq.) were then added, and the mixture was stirred at RT for a further 12 h. The reaction mixture was then filtered through kieselguhr, the filter residue was washed with dichloromethane and methanol and the filtrate was concentrated to dryness. The residue was purified by preparative HPLC (Gromsil C18 column, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). The product was obtained as a colorless solid (14.6 mg, 19% of theory).

Workup

  1. stirringthe mixture was stirred at RT for a further 12 h
  2. filtrationThe reaction mixture was then filtered through kieselguhr
  3. washthe filter residue was washed with dichloromethane and methanol
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe residue was purified by preparative HPLC (Gromsil C18 column, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10)
  6. customThe product was obtained as a colorless solid (14.6 mg, 19% of theory)

Sources & evidence

ORD record
ord-3a544a499df943299d1f3aee5746488c
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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