Triethylamine → HCID 70157266, compound

HRID 1278585Notes

Reaction equation

HRID 1278585 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=3)C(O)=O)[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:2].C([N:37](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C1(C)C=CC=CC=1.C(O)(C)(C)C>[CH2:1]([N:3]([CH2:33][CH3:34])[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:24]3[CH:32]=[CH:31][CH:30]=[C:26]([NH2:37])[CH:25]=3)[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18431021HCID 18431021, compound

Product 1

HCID 70157266HCID 70157266, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

To a stirring solution of 3-[4-(5-Diethylcarbamoyl-pyrimidin-2-yl)-1-(2-methyl-pentyl)-piperidin-4-yl]-benzoic acid (210 mg, 0.45 mmol) in 8 mL Toluene and 2 mL tert-butyl alcohol at room temperature was added triethylamine (0.066 mL, 0.48 mmol) and diphenylphosphoryl azide (0.07 mL, 0.45 mmol). The resulting mixture was heated at 120° C. for 20 hours, cooled to room temperature, washed with water, dried and concentrated. The resulting residue was taken up in EtOH/5N HCl (1:1) and stirred at room temperature for 22 hours. The resulting mixture was basified (pH=9) with NaOH and extracted with EtOAc (3×20 mL). The combined organic layers were dried and concentrated. Purification of the crude material was accomplished by flash chromatography with a solvent gradient of 5% and 10% MeOH/CH2Cl2 to yield 125 mg of the desired product. 1HNMR (400 MHz, CDCl3) δ 8.71 (s, 2H), 7.02 (t, 1H), 6.76 (d, 1H), 6.71 (s, 1H), 6.45 (d, 1H), 3.57-3.52 (comp, 4H), 3.28-3.26 (comp, 2H), 2.93-2.89 (comp, 2H), 2.71 (br s, 2H), 2.33 (br s, 2H), 2.15-1.96 (comp, 4H), 1.61 (br s, 1H), 1.38-1.17 (comp, 10H), 1.03-0.96 (comp, 1H), 0.86-0.83 (comp, 6H); MS (M+1) 438.6.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. extractionextracted with EtOAc (3×20 mL)
  6. customThe combined organic layers were dried
  7. concentrationconcentrated
  8. customPurification of the crude material

Sources & evidence

ORD record
ord-38c1a1d9f81b4f56b90cf151a353cf79
Source dataset
uspto-grants-2002_09
Patent number
US06444679B1

Reaction notes

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