Triethylamine → HCID 66819479, compound

HRID 880830Notes

Reaction equation

HRID 880830 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].[C:21]([O:25][C:26](=[O:32])[NH:27][CH2:28][CH2:29][CH2:30][NH2:31])([CH3:24])([CH3:23])[CH3:22].C(N(CC)CC)C>CN(C)C=O>[C:21]([O:25][C:26](=[O:32])[NH:27][CH2:28][CH2:29][CH2:30][NH:31][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)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 9814438N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)-chloroacetamide

Product 1

HCID 66819479HCID 66819479, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 50 mg of 2-chloro-N-(6-oxo-5,6-dihydro-phenanthridin-2-yl)acetamide (XV) (0.17 mmol) in N,N-dimethylformamide (3 mL), 0.09 mL of (3-amino-propyl)-carbamic acid tert-butyl ester (0.51 mmol) and 0.036 mL of triethylamine (0.26 mmol) were added. The reaction mixture was stirred at room temperature overnight, evaporated to dryness and then purified through preparative HPLC on a Waters X Terra RP 18 (19×250 mm, 5 □m) column. Mobile phase A was 0.05% ammonia/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 32 mg (44% yield) of the title compound.

Workup

  1. additionwere added
  2. customevaporated to dryness
  3. custompurified through preparative HPLC on a Waters X Terra RP 18 (19×250 mm, 5 □m) column
  4. waitGradient from 10 to 75% B in 15 min
  5. additionFractions containing the desired compound
  6. customwere dried

Sources & evidence

ORD record
ord-c998bd6d726a43fda89d350c52f3b852
Source dataset
uspto-grants-2015_03
Patent number
US08993594B2

Reaction notes

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