Sodium Chloride → 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(1-methyl-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide

HRID 2364668Notes

Reaction equation

HRID 2364668 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:26]([OH:28])=O)=[C:21]5[C:25]=4[O:24][CH2:23][CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:29])[C:8](=[O:30])[C@H:7]2[CH2:31][CH3:32])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.[N:38]1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH3:64][N:65]1[CH2:70][CH2:69][CH:68](N)[CH2:67][CH2:66]1.[Cl-].[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:26]([NH:38][CH:66]5[CH2:67][CH2:68][CH2:69][CH2:70][N:65]5[CH3:64])=[O:28])=[C:21]5[C:25]=4[O:24][CH2:23][CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:29])[C:8](=[O:30])[C@H:7]2[CH2:31][CH3:32])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27375314-Amino-1-methylpiperidineHCID 681074757-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid

Product 1

HCID 681077787-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-(1-methyl-piperidyl)-2,3-dihydrobenzofuran-4-carboxamideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,3-dihydrobenzofuran-4-carboxylic acid 1q (300 mg, 0.68 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (148 mg, 0.46 mmol) were dissolved in 30 mL of dichloromethane, followed by the addition of diisopropylethylamine (131 mg, 1 mmol). The reaction solution was stirred for 10 minutes followed by the addition of 1-methyl-piperidin-4-yl amine (52 mg, 0.46 mmol), and stirred for another 3 hours. The reaction mixture was added with 30 mL of saturated sodium chloride solution and 30 mL of dichloromethane successively, then seperated. The organic phase was washed with saturated sodium carbonate solution (50 mL×2), water (50 mL) and saturated sodium chloride solution (50 mL) successively, then dried over anhydrous sodium 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]-N-(1-methyl-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide 1 (194 mg, yield: 79%) as a white solid.

Workup

  1. stirringstirred for another 3 hours
  2. customseperated
  3. washThe organic phase was washed with saturated sodium carbonate solution (50 mL×2), water (50 mL) and saturated sodium chloride solution (50 mL) successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-85f208e874bb4580865e19bd1cbf6823
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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