Triethylamine → (6-{[(6-Oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-hexyl)-carbamic acid tert-butyl ester

HRID 1618119Notes

Reaction equation

HRID 1618119 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=1)=[O:4].Cl.[C:22]([O:26][C:27](=[O:36])[NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>CN(C)C=O.ClCCl>[C:22]([O:26][C:27](=[O:36])[NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][CH2:2][C:3](=[O:4])[NH:5][C:6]1[CH:19]=[CH:18][C:17]2[NH:16][C:15](=[O:20])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3017638N-Boc-1,6-diamino-hexane hydrochlorideHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide

Product 1

HCID 66819636(6-{[(6-Oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-hexyl)-carbamic acid tert-butyl esterYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-chloro-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-acetamide (XXIV, Lg=Cl) (65 mg, 0.23 mmol) in N,N-dimethylformamide (2 mL), (6-amino-hexyl)-carbamic acid tert-butyl ester hydrochloride (175 mg, 0.69 mmol) and triethylamine (0.097 mL, 0.69 mmol) were added. The reaction mixture was stirred at room temperature overnight, diluted with dichloromethane, and the resulting solution was washed with water then brine, dried over sodium sulfate and evaporated to dryness. The crude was purified by preparative HPLC on Waters X Terra RP 18 (19×250 mm, 5 μm) column. Mobile phase A was 0.05% ammonium hydroxide/acetonitrile:95/5 and mobile phase B was acetonitrile/water:95/5. Gradient from 10 to 75% B in 15 min. Fractions containing the desired compound were dried, affording 50 mg (47% yield) of (6-{[(6-oxo-5,6-dihydro-phenanthridin-2-ylcarbamoyl)-methyl]-amino}-hexyl)-carbamic acid tert-butyl ester.

Workup

  1. additionwere added
  2. washthe resulting solution was washed with water
  3. dry with materialbrine, dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe crude was purified by preparative HPLC on Waters X Terra RP 18 (19×250 mm, 5 μm) column
  6. waitGradient from 10 to 75% B in 15 min
  7. additionFractions containing the desired compound
  8. customwere dried

Sources & evidence

ORD record
ord-e3e74a8fd4354f9fa6aa968f3ee97d1c
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

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