Triethylamine → HCID 68838775, compound

HRID 1454152Notes

Reaction equation

HRID 1454152 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:18]1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41][CH2:42][CH:43](O)[CH2:44][CH2:45][CH2:46][C:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=2)[CH:35]=1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:18][CH:43]([CH2:44][CH2:45][CH2:46][C:47]2[CH:48]=[N:49][CH:50]=[CH:51][CH:52]=2)[CH2:42][CH2:41][CH2:40][C:36]2[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15838413HCID 15838413, compound

Product 1

HCID 68838775HCID 68838775, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-tert-Butoxycarbonyl-piperidine-4-carboxylic acid (0.5 g; 2.18 mmol) is dissolved in DMF (10 mL) at ambient temperature. 1-Hydroxybenzotriazole (0.37, 2.74 mmol), triethylamine (0.46 mL, 3.3 mmol), 1,7-di-(3-pyridyl)-heptan-4-ol (0.59 g; 2.4 mmol) as prepared according to WO 98/20893 A1 assigned to Vertex Pharmaceuticals, and N-(3-dimethylamino-propyl)-N′-ethylcarbodiimide hydrochloride (0.46 g; 2.4 mmol) are added sequentially. The mixture is stirred at ambient temperature for 18 hours. The mixture is then poured onto ethyl acetate (150 mL) and washed successively with water (50 mL), saturated aqueous sodium bicarbonate (10 mL), and brine (30 mL). The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The residue is purified via silica gel chromatography with gradient elution (0%→25% methanol in methylene chloride) affording the desired product (0.3754 g) as a yellow solid. ESMS: MH+ 482.4.

Workup

  1. additionare added sequentially
  2. additionThe mixture is then poured onto ethyl acetate (150 mL)
  3. washwashed successively with water (50 mL), saturated aqueous sodium bicarbonate (10 mL), and brine (30 mL)
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified via silica gel chromatography with gradient elution (0%→25% methanol in methylene chloride)

Sources & evidence

ORD record
ord-9d7ca98b659a4d6085b8638b4f2d02d8
Source dataset
uspto-grants-2009_01
Patent number
US07476680B2

Reaction notes

Loading…