Diisopropylethylamine → HCID 51036182, compound

HRID 2364734Notes

Reaction equation

HRID 2364734 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:27]([OH:29])=O)=[C:21]5[C:25]=4[O:24][CH:23]([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:30])[C:8](=[O:31])[C@H:7]2[CH2:32][CH3:33])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[B-](F)(F)F.[N:39]1(OC(N(C)C)=[N+](C)C)[C:43]2[CH:44]=[CH:45]C=[CH:47][C:42]=2N=N1.[CH:56]([N:59](C(C)C)CC)(C)C.C(=O)(O)[O-].[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:27]([NH:39][CH:43]5[CH2:42][CH2:47][N:59]([CH3:56])[CH2:45][CH2:44]5)=[O:29])=[C:21]5[C:25]=4[O:24][CH:23]([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:30])[C:8](=[O:31])[C@H:7]2[CH2:32][CH3:33])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68107395HCID 68107395, compound

Product 1

HCID 51036182HCID 51036182, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2-methyl-2,3-dihydrobenzofuran-4-carboxylic acid 30d (70 mg, 0.20 mmol), 1-methyl-piperidyl-4-yl-amine (23 mg, 0.20 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (64 mg, 0.20 mmol) and diisopropylethylamine (65 mg, 0.50 mmol) were dissolved in 30 mL of dichloromethane. The reaction solution was stirred for 2 hours. The resulting solution was added with 20 mL of saturated sodium bicarbonate solution and extracted with dichloromethane (50 mL×3). The combined organic phase was washed with water (30 mL) and saturated sodium chloride solution (30 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-methyl-N-(1-methyl-4-piperidyl)-2,3-dihydrobenzofuran-4-carboxamide 30 (40 mg, yield: 36.0%) as a white solid.

Workup

  1. extractionextracted with dichloromethane (50 mL×3)
  2. washThe combined organic phase was washed with water (30 mL) and saturated sodium chloride solution (30 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-7924224755a8488a9bd195c292eaa4e3
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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