Triethylamine → HCID 58926748, compound

HRID 2378118Notes

Reaction equation

HRID 2378118 reaction equation
[Cl:1][C:2]([O:4]C(Cl)(Cl)Cl)=O.[F:9][C:10]([F:46])([F:45])[C:11]1[CH:12]=[C:13]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=1)[CH2:14][N:15]([C@@H:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([F:35])([F:34])[F:33])[N:30]=2)[NH:25][C@H:24]([CH2:36][CH3:37])[CH2:23]1)[C:16]1[N:17]=[N:18][N:19]([CH3:21])[N:20]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:46][C:10]([F:9])([F:45])[C:11]1[CH:12]=[C:13]([CH:38]=[C:39]([C:41]([F:42])([F:43])[F:44])[CH:40]=1)[CH2:14][N:15]([C:16]1[N:17]=[N:18][N:19]([CH3:21])[N:20]=1)[C@@H:22]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([C:32]([F:33])([F:34])[F:35])[N:30]=2)[N:25]([C:2]([Cl:1])=[O:4])[C@H:24]([CH2:36][CH3:37])[CH2:23]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 10426Diphosgene2×HCID 58926723HCID 58926723, compound

Product 1

HCID 58926748HCID 58926748, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add trichloromethyl chloroformate (0.36 mL, 3.02 mmol) to a solution of (2R,4S)-(3,5-Bis-trifluoromethyl-benzyl)-(2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-[1,5]naphthyridin-4-yl)-(2-methyl-2H-tetrazol-5-yl)-amine (1.67 g, 3.02 mmol) and triethylamine (0.84 mL, 6.04 mmol) in toluene (19 mL). Stir the mixture at room temperature under nitrogen for 3 h, then add more triethylamine (0.50 mL, 3.6 mmol) and trichloromethyl chloroformate (0.21 mL, 1.8 mmol). Stir the mixture overnight. Evaporate the solvent and purify the residue by silica gel chromatography (elution with hexane/ethyl acetate) to afford the title compound (1.83 g, 98%). MS (ES+): 616 (M+H).

Workup

  1. stirringStir the mixture overnight
  2. customEvaporate the solvent
  3. custompurify the residue
  4. washby silica gel chromatography (elution with hexane/ethyl acetate)

Sources & evidence

ORD record
ord-174b809141f3408f979cd2ee06c1f6f0
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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