Triethylamine → HCID 86700733, compound

HRID 2370086Notes

Reaction equation

HRID 2370086 reaction equation
F[C:2]1[CH:3]=CC(O[C@H]2CC[C@H](C(O)=O)CC2)=N[CH:7]=1.C(Cl)(=O)C(Cl)=O.COC(C1C=C(C=CC=1)O[C@H]1CC[C@H](C([N:40](C)[C:41]2[CH:61]=[CH:60][C:44]([CH2:45][N:46]3[CH2:51][CH2:50][N:49]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C@@H:48](C)[CH2:47]3)=[C:43]([CH3:62])[CH:42]=2)=O)CC1)=O.C(N(CC)CC)C>ClCCl.CN(C)C=O>[CH:2]([NH:40][C:41]1[CH:61]=[CH:60][C:44]([CH2:45][N:46]2[CH2:47][CH2:48][N:49]([C:52]([O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:53])[CH2:50][CH2:51]2)=[C:43]([CH3:62])[CH:42]=1)([CH3:3])[CH3:7]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178497970HCID 178497970, compoundHCID 178525772HCID 178525772, compound

Product 1

HCID 86700733HCID 86700733, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyl trans-4-[(5-fluoropyridin-2-yl)oxy]cyclohexanecarboxylate (511 mg, 1.73 mmol) produced in (15B) was dissolved in dichloromethane (5 mL), and trifluoroacetic acid (2 mL) was added thereto at 0° C., and then, the resulting mixture was stirred under a nitrogen atmosphere for 2 hours. After toluene (10 mL) was added to the reaction solution, the solvent was distilled off under reduced pressure, followed by drying, whereby trans-4-[(5-fluoropyridin-2-yl)oxy]cyclohexanecarboxylic acid was obtained as a colorless oil (310 mg, yield: 74%). The obtained trans-4-[(5-fluoropyridin-2-yl)oxy]cyclohexanecarboxylic acid (310 mg, 0.892 mmol) was dissolved in dichloromethane (5 mL), and oxalyl chloride (235 μL, 2.68 mmol) and a catalytic amount of dimethylformamide were added thereto at 0° C., and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 30 minutes. The residue obtained by distilling off the solvent in the reaction solution under reduced pressure was dissolved in dichloromethane (15 mL), and tert-butyl 4-[4-(isopropylamino)-2-methylbenzyl]piperazine-1-carboxylate (113 mg, 0.325 mmol) produced in (5A) and triethylamine (125 μL, 0.892 mmol) were added thereto at 0° C., and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 1 hour.

Workup

  1. customThe residue obtained
  2. distillationby distilling off the solvent in the reaction solution under reduced pressure
  3. dissolutionwas dissolved in dichloromethane (15 mL)

Sources & evidence

ORD record
ord-b7779b1ffe5d424eb51366358652f552
Source dataset
uspto-grants-2014_04
Patent number
US08710060B2

Reaction notes

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