Triethylamine → HCID 123642442, compound

HRID 535501Notes

Reaction equation

HRID 535501 reaction equation
O.Cl.[NH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[NH:7][N:6]=1.[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[C:20]([O:19][C:17](=[O:16])[NH:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[NH:7][N:6]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 86812154HCID 86812154, compound

Product 1

HCID 123642442HCID 123642442, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(aminomethyl)phthalazin-1(2H)-one hydrochloride hydrate (0.300 g, 1.31 mmol), BOC2O (0.314 g, 1.44 mmol), and triethylamine (0.46 mL, 3.3 mmol) in DCM (4.5 mL) was stirred for 2 hours, diluted with EtOAc, washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and chromatographed (70% EtOAc/hexanes) to give 313 mg of the title compound as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 12.62-12.50 (m, 1H), 8.30-8.22 (m, 1H), 8.01 (s, 1H), 7.92 (dd, J=11.0, 4.1, 1H), 7.89-7.80 (m, 1H), 7.41-7.26 (m, 1H), 4.44 (d, J=5.8, 2H), 1.39 (s, 9H).

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customchromatographed (70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9f15c02941ff4f28a0921f6f2e3de59a
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

Loading…