Dimethylamine → HCID 22050400, compound

HRID 1831959Notes

Reaction equation

HRID 1831959 reaction equation
[Br:1][C:2]1[C:3](=[O:40])[N:4]([CH2:19][C:20]2[CH:21]=[C:22]([CH:37]=[CH:38][CH:39]=2)[CH2:23][NH:24][C:25](=[O:36])OC2C=CC([N+]([O-])=O)=CC=2)[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17].[CH3:41][NH:42][CH3:43]>ClCCl.O1CCCC1>[Br:1][C:2]1[C:3](=[O:40])[N:4]([CH2:19][C:20]2[CH:21]=[C:22]([CH:37]=[CH:38][CH:39]=2)[CH2:23][NH:24][C:25](=[O:36])[N:42]([CH3:43])[CH3:41])[C:5]([CH3:18])=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[F:17]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 22050691HCID 22050691, compound

Product 1

HCID 22050400HCID 22050400, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a reaction vessel (borosilicate culture tube) was added 4-nitrophenyl 3-{[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]methyl}benzylcarbamate (from step 1) (0.350 g, 0.570 mmol) dissolved in dichloromethane (6.0 mL). The parallel reaction apparatus was then orbitally shaken (Labline Benchtop Orbital Shaker) at approximately 200 RPM at room temperature for 15 minutes. A stock solution of N,N-dimethylamine in tetrahydorfuran (0.427 mL, 2.0 M) was then added to the reaction vessel and the reaction apparatus was orbitally shaken at room temperature overnight. The reaction mixture was concentrated and subjected to chromatography (silica gel, ethyl acetate with 10% methanol/hexanes) which afforded an off white solid (0.226 g, 63.3%). 1H NMR (400 MHz, DMF-d6) δ 7.81 (app q, J=7.92 Hz, 1H), 7.40-7.19 (m, 5H), 7.06 (d, J=7.45 Hz, 1H), 6.88 (app t, J=5.84 Hz, 1H), 6.68 (s, 1H), 5.45 (s, 2H), 5.42 (s, 1H), 4.35 (d, J=5.84 Hz, 1H), 2.92 (s, 6H), 2.44 (s, 3H). ES-HRMS m/z 520.1065 (M+H C24H24BrF2N3O3 requires 520.1042).

Workup

  1. stirringthe reaction apparatus was orbitally shaken at room temperature overnight
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-d4a2690969ae438db1fb1d09d1700739
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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