Methylamine → HCID 22050383, compound

HRID 1867125Notes

Reaction equation

HRID 1867125 reaction equation
[Br:1][C:2]1[C:3](=[O:29])[N:4]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=2[F:28])[C:22](O)=[O:23])[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].O[N:31]1[C:35]2C=CC=C[C:34]=2[N:33]=N1.N=C=N.[CH3:43]N.CN=C=O.O1CC[CH2:51][CH2:50]1>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:29])[N:4]([C:19]2[CH:20]=[C:21]([C:22]([N:33]3[CH2:34][CH2:35][N:31]([CH3:43])[CH2:51][CH2:50]3)=[O:23])[CH:25]=[CH:26][C:27]=2[F:28])[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

8

Reactant 6

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 12228Methyl IsocyanateHCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 22050518HCID 22050518, compound

Product 1

HCID 22050383HCID 22050383, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a reaction vessel (borosilicate culture tube) was added 3-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]-4-fluorobenzoic acid (0.300 g, 0.623 mmol) and 1-hydroxybenzotriazole (0.042 g, 0.45 mmol). N,N-Dimethylformamide (3 mL) was added to the reaction vessel followed by approximately 1.1 g of the polymer bound carbodiimide resin (1.38 mmol/g). Additional N,N-dimethylformamide (2 mL) was then added to the reaction vessel. The parallel reaction apparatus was then orbitally shaken (Labline Benchtop Orbital Shaker) at approximately 200 RPM at room temperature for 15 minutes. N-Methyl amine (1 mL, 2 mmol) was then added to the reaction vessel and the reaction apparatus was orbitally shaken at room temperature overnight. At this time the reaction was diluted with tetrahydrofuran (20 mL) and treated with approximately 2.0 g of polyamine resin (2.63 mmol/g) and approximately 2.5 g of methylisocyanate functionalized polystyrene (1.5 mmol/g) and the orbital shaking was continued at 200 RPM at room temperature for 3 hours. The reaction vessel was then opened and the solution phase product was separated from the insoluble quenched byproducts by filtration and collection into a vial. After partially evaporation the insoluble byproducts were rinsed with tetrahydrofuran (2×10 mL). The filtrate was evaporated by blowing N2 over the vial and the resulting solid was triturated with diethyl ether to give an off-white solid. (0.14 g, 41%)

Workup

  1. stirringthe reaction apparatus was orbitally shaken at room temperature overnight
  2. stirringthe orbital shaking
  3. waitwas continued at 200 RPM at room temperature for 3 hours
  4. customthe solution phase product was separated from the insoluble quenched byproducts by filtration and collection into a vial
  5. customAfter partially evaporation the insoluble byproducts
  6. washwere rinsed with tetrahydrofuran (2×10 mL)
  7. customThe filtrate was evaporated
  8. customwas triturated with diethyl ether
  9. customto give an off-white solid

Sources & evidence

ORD record
ord-c04bb29388bb4e4689eaa36a20178c9a
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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