Pyridine → HCID 46840938, compound

HRID 1046838Notes

Reaction equation

HRID 1046838 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[N:17]=[C:13]3[NH:12][C:11]([CH3:25])=[C:10]2[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:5][CH:4]=1)#[N:2].[F:31][C:32]([F:43])([F:42])[C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1.N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:22])([F:21])[F:23])[N:17]=[C:13]3[N:12]([C:37]3[CH:36]=[CH:35][CH:34]=[C:33]([C:32]([F:43])([F:42])[F:31])[CH:38]=3)[C:11]([CH3:25])=[C:10]2[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acid2×HCID 136133154HCID 136133154, compound

Product 1

HCID 46840938HCID 46840938, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

Ethyl 7-(4-cyanophenyl)-5-methyl-2-[(trifluoroacetyl)amino]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (45 mg, 107 μmol) and 3-(trifluoromethyl)phenylboronic acid (61 mg, 321 μmol, 3 eq.) were initially charged together with anhydrous copper(II) acetate (58 mg, 321 μmol, 3 eq.) and molecular sieve (0.1 g, 4 Å) and, under an atmosphere of argon protective gas, suspended in abs. dichloromethane (3 ml). Abs. pyridine (69 μl, 856 μmol, 8 eq.) and triethylamine (45 μl, 321 μmol, 3 eq.) were then added. After 12 h of stirring, more 3-(trifluoromethyl)phenylboronic acid (20 mg, 107 μmol, 1 eq.), anhydrous copper(II) acetate (19 mg, 321 μmol, 1 eq.) and pyridine (35 μl, 428 μmol, 4 eq.) were added, and the mixture was stirred for a further 24 h. The mixture was then filtered through kieselguhr, the filter residue was washed with dichloromethan and methanol and the filtrate concentrated under reduced pressure. The residue was purified by preparative HPLC (Gromsil C18 column, 10 μm, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (10.3 mg, 17% of theory).

Workup

  1. stirringthe mixture was stirred for a further 24 h
  2. filtrationThe mixture was then filtered through kieselguhr
  3. washthe filter residue was washed with dichloromethan and methanol
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC (Gromsil C18 column, 10 μm, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  6. customAfter lyophilization, the product was obtained as a solid (10.3 mg, 17% of theory)

Sources & evidence

ORD record
ord-1775cf6171884604b941f3bc4479429c
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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