Pyridine → HCID 86613789, compound

HRID 2378110Notes

Reaction equation

HRID 2378110 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH:8]([O:11][C:12]([N:14]1[C:23]2[C:18](=[N:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[C@H:17]([NH:26][CH2:27][C:28]2[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=2)[CH2:16][C@@H:15]1[CH2:42][CH3:43])=[O:13])([CH3:10])[CH3:9].N1C=CC=CC=1>ClCCl>[CH:8]([O:11][C:12]([N:14]1[C:23]2[C:18](=[N:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[C@H:17]([N:26]([C:1](=[O:3])[CH3:2])[CH2:27][C:28]2[CH:33]=[C:32]([C:34]([F:35])([F:36])[F:37])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=2)[CH2:16][C@@H:15]1[CH2:42][CH3:43])=[O:13])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86613791HCID 86613791, compound

Product 1

HCID 86613789HCID 86613789, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add acetic anhydride (0.023 mL, 1.205 mmol) to a solution of (+/−)-cis-4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (125 mg, 0.241 mmol) and pyridine (0.097 mL, 1.205 mmol) in dichloromethane (2 mL), and stir at room temperature for 14 h. Remove the solvent under reduced pressure and purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (105 mg, 78%). 1H NMR (CDCl3, 300 MHz): δ 0.66-0.72 (m, 3H), 1.20-1.29 (m, 7H), 1.33-1.69 (m, 3H), 2.01-2.21 (m, 3H), 2.26-2.33 (m, 1H), 3.82, 3.86 (s, 3H), 4.22-4.28 (m, 1H), 4.81-5.01 (m, 2H), 6.59, 6.65 (d, J=8.7 Hz, 1H), 7.61-7.73 (m, 4H). MS (ES+): 562 (M+H).

Workup

  1. customRemove the solvent under reduced pressure
  2. custompurify the residue by flash chromatography
  3. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b76b0e0a037f49ac96479e073895e51c
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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