Triethylamine → HCID 68541519, compound

HRID 1446026Notes

Reaction equation

HRID 1446026 reaction equation
Cl.Cl.[CH2:3]([NH:5][CH2:6][CH2:7][CH2:8]N(C)C)[CH3:4].[CH2:12]([N:14](CC)[CH2:15]C)C.[CH3:19][C:20]([O:22][C@H:23]1[C:32]2[C@@:33]3([CH3:48])[C@@H:44]([CH2:45][O:46][CH3:47])[O:43][C:41](=[O:42])[C:35]4=[CH:36][O:37][C:38]([C:39](=[O:40])[C:31]=2[C@@H:26]2[CH2:27][CH2:28][C@H:29]([OH:30])[C@@:25]2([CH3:49])[CH2:24]1)=[C:34]34)=[O:21]>ClCCl>[CH3:12][N:14]([CH3:15])[CH:7]([CH3:8])[CH2:6][N:5]([CH:36]=[C:35]1[C:34]2[C:33]([CH3:48])([C:32]3[CH:23]([O:22][C:20](=[O:21])[CH3:19])[CH2:24][C:25]4([CH3:49])[CH:26]([C:31]=3[C:39](=[O:40])[C:38]=2[OH:37])[CH2:27][CH2:28][CH:29]4[OH:30])[CH:44]([CH2:45][O:46][CH3:47])[O:43][C:41]1=[O:42])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 986734017beta-Hydroxy wortmanninHCID 86605520HCID 86605520, compound

Product 1

HCID 68541519HCID 68541519, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the (3-dimethylaminopropyl)-ethyl-carbamic acid benzyl ester trifluoroacetate (0.84 g, 2.2 mmol) in ethanol (30 mL) and concentrated hydrochloric acid (0.5 mL, 6 mmol) was added palladium on carbon (10%, 50 mg). The suspension was shaken under 50 psi hydrogen. When the consumption of hydrogen was observed to have ceased, the mixture was filtered through a pad of diatomaceous earth and then concentrated under reduced pressure to give N′-ethyl-N,N-dimethylpropane-1,3-diamine dihydrochloride (400 mg, 89%) as a white solid. MS (ES+): m/z (M+H)=131.3 To a suspension of the N′-ethyl-N,N-dimethylpropane-1,3-diamine dihydrochloride (0.26 g, 1.3 mmol) in dichloromethane (5 mL) was added triethylamine (0.51 mL, 3.9 mmol). After stirring for 10 minutes, the mixture was treated with 17-hydroxywortmannin (0.28 g, 0.65 mmol). After stirring overnight at room temperature, the mixture was concentrated under reduced pressure and then purified by reverse-phase HPLC (employing a gradient elution of 5% acetonitrile/95% water to 95% acetonitrile over 45 minutes). The title compound was obtained as a rust-colored solid (11.6 mg). MS (ES+): m/z (M+H)=561.4.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. custompurified by reverse-phase HPLC (
  4. washa gradient elution of 5% acetonitrile/95% water to 95% acetonitrile over 45 minutes)

Sources & evidence

ORD record
ord-822e416b537e466588125a04194f96c3
Source dataset
uspto-grants-2010_02
Patent number
US07666901B2

Reaction notes

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