Sodium Chloride → HCID 51036181, compound

HRID 2364730Notes

Reaction equation

HRID 2364730 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:30](O)=[O:31])=[C:21]5[C:25]=4[O:24][CH:23]([CH2:26][N:27]([CH3:29])[CH3:28])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:33])[C:8](=[O:34])[C@H:7]2[CH2:35][CH3:36])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.[N:42]1(OC(N(C)C)=[N+](C)C)[C:46]2[CH:47]=[CH:48]C=[CH:50][C:45]=2N=N1.[CH:59]([N:62](C(C)C)CC)(C)C.[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:30]([NH:42][CH:46]5[CH2:45][CH2:50][N:62]([CH3:59])[CH2:48][CH2:47]5)=[O:31])=[C:21]5[C:25]=4[O:24][CH:23]([CH2:26][N:27]([CH3:29])[CH3:28])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:33])[C:8](=[O:34])[C@H:7]2[CH2:35][CH3:36])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68107370HCID 68107370, compound

Product 1

HCID 51036181HCID 51036181, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-(dimethylaminomethyl)-2,3-dihydrobenzofuran-4-carboxylic acid 29j (30 mg, 0.06 mmol) was dissolved in 10 mL of dichloromethane followed by the addition of 1-methyl-piperidyl-4-yl-amine (7 mg, 0.06 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (20 mg, 0.06 mmol) and diisopropylethylamine (24 mg, 0.18 mmol). The reaction solution was stirred for 2 hours. The resulting solution was added with 10 mL of saturated sodium chloride solution and extracted with dichloromethane (10 mL×3). The combined organic phase was washed with water (10 mL) and saturated sodium chloride solution (10 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-(dimethylaminomethyl)-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide 29 (27 mg, yield: 77.1%) as a white solid.

Workup

  1. extractionextracted with dichloromethane (10 mL×3)
  2. washThe combined organic phase was washed with water (10 mL) and saturated sodium chloride solution (10 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-a3afb8f030544595be1934d0ca3b73f2
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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