Sodium Carbonate → HCID 51036787, compound

HRID 2364753Notes

Reaction equation

HRID 2364753 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:29]([OH:31])=O)=[C:21]5[C:25]=4[O:24][CH:23]([CH2:26][O:27][CH3:28])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:32])[C:8](=[O:33])[C@H:7]2[CH2:34][CH3:35])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.[N:41]1(OC(N(C)C)=[N+](C)C)[C:45]2[CH:46]=[CH:47]C=[CH:49][C:44]=2N=N1.[CH:58]([N:61](C(C)C)CC)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:29]([NH:41][CH:45]5[CH2:44][CH2:49][N:61]([CH3:58])[CH2:47][CH2:46]5)=[O:31])=[C:21]5[C:25]=4[O:24][CH:23]([CH2:26][O:27][CH3:28])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:32])[C:8](=[O:33])[C@H:7]2[CH2:34][CH3:35])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68107050HCID 68107050, compound

Product 1

HCID 51036787HCID 51036787, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-(methoxymethyl)-2,3-dihydrobenzofuran-4-carboxylic acid 40e (50 mg, 0.10 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (33 mg, 0.10 mmol) were dissolved in 40 mL of dichloromethane followed by the addition of diisopropylethylamine (38 μL, 0.23 mmol) and 1-methyl-piperidyl-4-yl-amine (12 mg, 0.10 mmol) successively. The reaction solution was stirred for 1 hour, added with 20 mL of saturated sodium carbonate solution and extracted with dichloromethane (30 mL×3). The combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively, then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-(methoxymethyl)-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide 40 (40 mg, yield: 69.0%) as a light yellow solid.

Workup

  1. extractionextracted with dichloromethane (30 mL×3)
  2. washThe combined organic phase was washed with water (20 mL) and saturated sodium chloride solution (20 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dd70c0e9296a450b97ab6d4a84e061d3
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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