Methyl chloroformate → HCID 86669802, compound

HRID 1876839Notes

Reaction equation

HRID 1876839 reaction equation
[C:1]1([C@@H:7]2[C:12]3=[CH:13][C:14]([NH2:26])=[N:15][C:16]4[C@@H:17]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:18][CH2:19][N:10]([C:11]=43)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:35]([O:37][CH3:38])=[O:36]>ClCCl>[C:1]1([C@@H:7]2[C:12]3=[CH:13][C:14]([NH:26][C:35](=[O:36])[O:37][CH3:38])=[N:15][C:16]4[C@@H:17]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:18][CH2:19][N:10]([C:11]=43)[CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67022710HCID 67022710, compound2×

Product 1

HCID 86669802HCID 86669802, compoundYield 15.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (4R,10R)-4,10-diphenyl-4,5,6,8,9,10-hexahydropyrido[3,2,1-de][1,5]naphthyridin-2-amine (Intermediate 4), (110 mg, 0.322 mmol) in dichloromethane (10 mL) was added two equivalent of triethyl amine (0.090 mL, 0.644 mmol), followed by methyl chloroformate (0.037 mL, 0.483 mmol) under argon at 0° C. The reaction mixture was then stirred at room temperature for overnight. The mixture was quenched with water (30 mL). The residue was isolated in a typical aqueous workup and purified by MPLC (medium pressure liquid chromatography) using silica gel column with 10 to 15% EtOAc:Hexane to give methyl (4R,10R)-4,10-diphenyl-4,5,6,8,9,10-hexahydropyrido[3,2,1-de][1,5]naphthyridin-2-ylcarbamate, (179), (20 mg). 1H NMR (300 MHz, CDCl3) δ ppm 2.00-2.18 (m, 2H) 2.22-2.39 (m, 2H) 3.03-3.22 (m, 4H) 3.50-3.64 (m, 3H) 3.54-3.65 (m, 3H) 4.05-4.23 (m, 2H) 6.61 (br. s., 2H) 7.08-7.38 (m, 10H)

Workup

  1. customThe mixture was quenched with water (30 mL)
  2. customThe residue was isolated in a typical aqueous workup
  3. custompurified by MPLC (medium pressure liquid chromatography)

Sources & evidence

ORD record
ord-d698c4eeadf44fd5a064c11c7dc3e3f7
Source dataset
uspto-grants-2012_11
Patent number
US08309729B2

Reaction notes

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